# Electronic Supplementary Material (ESI) for Dalton Transactions.
# This journal is © The Royal Society of Chemistry 2015

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_mbb_088
_database_code_depnum_ccdc_archive 'CCDC 1424212'
_audit_update_record             
;
2015-09-14 deposited with the CCDC.
2015-11-09 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         'C46 H42 Cl Cu N10 O2, Cl2 Cu'
_chemical_formula_sum            'C46 H42 Cl3 Cu2 N10 O2'
_chemical_melting_point          ?

_exptl_crystal_description       prism
_exptl_crystal_colour            yellow

_diffrn_ambient_temperature      150(2)
_chemical_formula_weight         1000.33

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   'P -1'
_symmetry_int_tables_number      2
_chemical_absolute_configuration ?
_symmetry_space_group_name_Hall  '-P 1'

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   9.1159(2)
_cell_length_b                   13.6244(3)
_cell_length_c                   18.4950(4)
_cell_angle_alpha                74.0080(10)
_cell_angle_beta                 85.5160(10)
_cell_angle_gamma                89.2250(10)
_cell_volume                     2201.32(8)
_cell_formula_units_Z            2
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    9033
_cell_measurement_theta_min      2.30
_cell_measurement_theta_max      26.52
_exptl_crystal_size_max          0.42
_exptl_crystal_size_mid          0.35
_exptl_crystal_size_min          0.21
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.509
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1026
_exptl_absorpt_coefficient_mu    1.200

_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6326
_exptl_absorpt_correction_T_max  0.7867
_exptl_absorpt_process_details   'SADABS (Bruker, 2004)'

_exptl_special_details           
; 
 ? 
;


_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker Nonius X8Apex CCD area-detector'
_diffrn_measurement_method       'φ scans'
_diffrn_detector_area_resol_mean 25
_diffrn_standards_number         0
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        0
_diffrn_reflns_number            16421
_diffrn_reflns_av_R_equivalents  0.0179
_diffrn_reflns_av_sigmaI/netI    0.0262
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         1.66
_diffrn_reflns_theta_max         26.37
_reflns_number_total             8926
_reflns_number_gt                7770
_reflns_threshold_expression     >2σ(I)


_computing_data_collection       'APEX2 (Bruker, 2004)'
_computing_cell_refinement       'SAINT (Bruker, 2004)'
_computing_data_reduction        'SAINT (Bruker, 2004)'
_computing_structure_solution    'SHELXTL (Bruker, 2004)'
_computing_structure_refinement  'SHELXTL (Bruker, 2004)'
_computing_molecular_graphics    'SHELXTL (Bruker, 2004)'
_computing_publication_material  'SHELXTL (Bruker, 2004)'

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0471P)²+2.1831P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         8926
_refine_ls_number_parameters     578
_refine_ls_number_restraints     18
_refine_ls_R_factor_all          0.0461
_refine_ls_R_factor_gt           0.0385
_refine_ls_wR_factor_ref         0.1041
_refine_ls_wR_factor_gt          0.1001
_refine_ls_goodness_of_fit_ref   1.066
_refine_ls_restrained_S_all      1.574
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Cu1 Cu 0.55333(4) 0.41378(3) 0.14458(2) 0.02116(12) Uani 1 1 d . . .
Cu2 Cu 0.9885(5) 0.7636(5) 0.3639(3) 0.0617(3) Uani 0.199(3) 1 d PU A 2
Cl11 Cl 0.66563(10) 0.31947(7) 0.07521(5) 0.0323(2) Uani 1 1 d . . .
Cl21 Cl 1.0326(8) 0.6161(8) 0.4225(5) 0.0590(5) Uani 0.199(3) 1 d PU A 2
Cl22 Cl 0.9536(10) 0.9121(9) 0.2995(5) 0.0795(6) Uani 0.199(3) 1 d PU A 2
O11 O 0.1879(3) -0.0660(2) 0.54050(17) 0.0480(8) Uani 1 1 d . . .
O21 O 0.8902(4) 1.0156(3) -0.0739(2) 0.0674(11) Uani 1 1 d . . .
N11 N 0.6896(3) 0.43854(19) 0.23352(14) 0.0182(5) Uani 1 1 d . . .
N12 N 0.6140(3) 0.39039(18) 0.30097(13) 0.0167(5) Uani 1 1 d . . .
N13 N 0.4992(3) 0.29836(19) 0.23262(14) 0.0191(5) Uani 1 1 d . . .
N14 N 0.3621(3) 0.1458(2) 0.28911(16) 0.0258(6) Uani 1 1 d . . .
N15 N 0.3023(3) 0.0937(2) 0.41748(16) 0.0281(6) Uani 1 1 d . . .
N21 N 0.3755(3) 0.5030(2) 0.17614(15) 0.0217(5) Uani 1 1 d . . .
N22 N 0.4368(3) 0.5995(2) 0.16028(14) 0.0209(5) Uani 1 1 d . . .
N23 N 0.5906(3) 0.5490(2) 0.07178(14) 0.0215(5) Uani 1 1 d . . .
N24 N 0.7175(3) 0.6669(2) -0.03293(16) 0.0296(6) Uani 1 1 d . . .
N25 N 0.7106(4) 0.8405(3) -0.04651(19) 0.0431(8) Uani 1 1 d . . .
C11 C 0.7780(3) 0.5061(2) 0.24888(17) 0.0175(6) Uani 1 1 d . . .
C12 C 0.7588(3) 0.5027(2) 0.32616(17) 0.0199(6) Uani 1 1 d . . .
H12 H 0.8090 0.5432 0.3509 0.024 Uiso 1 1 calc R . .
C13 C 0.6540(3) 0.4297(2) 0.35825(17) 0.0184(6) Uani 1 1 d . . .
C14 C 0.5253(3) 0.3058(2) 0.30215(17) 0.0171(6) Uani 1 1 d . . .
C15 C 0.4708(4) 0.2363(2) 0.36656(17) 0.0212(6) Uani 1 1 d . . .
H15 H 0.4947 0.2399 0.4149 0.025 Uiso 1 1 calc R . .
C16 C 0.3769(4) 0.1584(2) 0.35842(18) 0.0219(6) Uani 1 1 d . . .
C17 C 0.4240(4) 0.2150(2) 0.23130(18) 0.0249(7) Uani 1 1 d . . .
H17 H 0.4145 0.2051 0.1830 0.030 Uiso 1 1 calc R . .
C21 C 0.2753(3) 0.4971(2) 0.23433(18) 0.0230(7) Uani 1 1 d . . .
C22 C 0.2755(4) 0.5880(3) 0.25668(18) 0.0256(7) Uani 1 1 d . . .
H22 H 0.2152 0.6025 0.2967 0.031 Uiso 1 1 calc R . .
C23 C 0.3792(4) 0.6515(3) 0.20971(18) 0.0241(7) Uani 1 1 d . . .
C24 C 0.5320(3) 0.6286(2) 0.09383(17) 0.0214(6) Uani 1 1 d . . .
C25 C 0.5588(4) 0.7284(3) 0.05501(19) 0.0276(7) Uani 1 1 d . . .
H25 H 0.5102 0.7829 0.0695 0.033 Uiso 1 1 calc R . .
C26 C 0.6631(4) 0.7458(3) -0.00816(19) 0.0306(8) Uani 1 1 d . . .
C27 C 0.6770(4) 0.5744(3) 0.00711(18) 0.0261(7) Uani 1 1 d . . .
H27 H 0.7128 0.5197 -0.0117 0.031 Uiso 1 1 calc R . .
C111 C 0.8786(3) 0.5713(2) 0.18928(17) 0.0191(6) Uani 1 1 d . . .
C112 C 0.9261(3) 0.6650(3) 0.19621(19) 0.0249(7) Uani 1 1 d . . .
H112 H 0.8947 0.6860 0.2398 0.030 Uiso 1 1 calc R . .
C113 C 1.0192(4) 0.7278(3) 0.1396(2) 0.0317(8) Uani 1 1 d . . .
H113 H 1.0492 0.7924 0.1439 0.038 Uiso 1 1 calc R . .
C114 C 1.0681(4) 0.6960(3) 0.0768(2) 0.0326(8) Uani 1 1 d . . .
H114 H 1.1328 0.7383 0.0384 0.039 Uiso 1 1 calc R . .
C115 C 1.0229(4) 0.6026(3) 0.0700(2) 0.0300(7) Uani 1 1 d . . .
H115 H 1.0571 0.5809 0.0271 0.036 Uiso 1 1 calc R . .
C116 C 0.9278(3) 0.5405(3) 0.12562(18) 0.0239(7) Uani 1 1 d . . .
H116 H 0.8962 0.4768 0.1203 0.029 Uiso 1 1 calc R . .
C131 C 0.5820(3) 0.3973(2) 0.43567(17) 0.0201(6) Uani 1 1 d . . .
C132 C 0.6594(4) 0.3468(3) 0.49633(19) 0.0306(8) Uani 1 1 d . . .
H132 H 0.7623 0.3365 0.4895 0.037 Uiso 1 1 calc R . .
C133 C 0.5850(5) 0.3111(3) 0.5675(2) 0.0433(10) Uani 1 1 d . . .
H133 H 0.6374 0.2758 0.6093 0.052 Uiso 1 1 calc R . .
C134 C 0.4364(5) 0.3266(3) 0.5775(2) 0.0431(10) Uani 1 1 d . . .
H134 H 0.3859 0.2999 0.6258 0.052 Uiso 1 1 calc R . .
C135 C 0.3600(4) 0.3809(3) 0.5179(2) 0.0366(9) Uani 1 1 d . . .
H135 H 0.2580 0.3936 0.5253 0.044 Uiso 1 1 calc R . .
C136 C 0.4329(4) 0.4166(3) 0.44708(19) 0.0265(7) Uani 1 1 d . . .
H136 H 0.3808 0.4544 0.4060 0.032 Uiso 1 1 calc R . .
C161 C 0.2875(4) 0.1061(3) 0.4940(2) 0.0338(8) Uani 1 1 d . . .
H16A H 0.1930 0.1397 0.5019 0.041 Uiso 1 1 calc R . .
H16B H 0.3683 0.1502 0.5003 0.041 Uiso 1 1 calc R . .
C162 C 0.2927(5) 0.0037(3) 0.5513(2) 0.0426(10) Uani 1 1 d . . .
H16C H 0.3925 -0.0250 0.5479 0.051 Uiso 1 1 calc R . .
H16D H 0.2735 0.0128 0.6026 0.051 Uiso 1 1 calc R . .
C163 C 0.2094(5) -0.0792(3) 0.4672(3) 0.0452(10) Uani 1 1 d . . .
H16E H 0.1359 -0.1288 0.4614 0.054 Uiso 1 1 calc R . .
H16F H 0.3085 -0.1076 0.4605 0.054 Uiso 1 1 calc R . .
C164 C 0.1950(4) 0.0198(3) 0.4073(2) 0.0353(8) Uani 1 1 d . . .
H16G H 0.2139 0.0087 0.3567 0.042 Uiso 1 1 calc R . .
H16H H 0.0940 0.0465 0.4112 0.042 Uiso 1 1 calc R . .
C211 C 0.1768(3) 0.4084(3) 0.26555(19) 0.0265(7) Uani 1 1 d . . .
C212 C 0.1188(4) 0.3871(3) 0.3406(2) 0.0367(9) Uani 1 1 d . . .
H212 H 0.1461 0.4280 0.3716 0.044 Uiso 1 1 calc R . .
C213 C 0.0208(4) 0.3057(4) 0.3698(2) 0.0473(12) Uani 1 1 d . . .
H213 H -0.0157 0.2897 0.4212 0.057 Uiso 1 1 calc R . .
C214 C -0.0233(5) 0.2485(3) 0.3248(3) 0.0513(13) Uani 1 1 d . . .
H214 H -0.0916 0.1938 0.3450 0.062 Uiso 1 1 calc R . .
C215 C 0.0314(5) 0.2702(3) 0.2502(3) 0.0499(11) Uani 1 1 d . . .
H215 H -0.0002 0.2310 0.2190 0.060 Uiso 1 1 calc R . .
C216 C 0.1325(4) 0.3493(3) 0.2207(2) 0.0361(9) Uani 1 1 d . . .
H216 H 0.1714 0.3630 0.1698 0.043 Uiso 1 1 calc R . .
C231 C 0.4301(4) 0.7518(3) 0.21410(18) 0.0260(7) Uani 1 1 d . . .
C232 C 0.3280(4) 0.8219(3) 0.2297(2) 0.0344(8) Uani 1 1 d . . .
H232 H 0.2256 0.8074 0.2332 0.041 Uiso 1 1 calc R . .
C233 C 0.3767(6) 0.9131(3) 0.2399(2) 0.0444(10) Uani 1 1 d . . .
H233 H 0.3070 0.9605 0.2508 0.053 Uiso 1 1 calc R . .
C234 C 0.5247(6) 0.9355(3) 0.2344(3) 0.0497(11) Uani 1 1 d . . .
H234 H 0.5567 0.9982 0.2413 0.060 Uiso 1 1 calc R . .
C235 C 0.6269(5) 0.8663(3) 0.2187(3) 0.0457(10) Uani 1 1 d . . .
H235 H 0.7291 0.8815 0.2147 0.055 Uiso 1 1 calc R . .
C236 C 0.5795(4) 0.7750(3) 0.2089(2) 0.0343(8) Uani 1 1 d . . .
H236 H 0.6498 0.7276 0.1985 0.041 Uiso 1 1 calc R . .
C261 C 0.6547(6) 0.9340(3) -0.0307(3) 0.0506(11) Uani 1 1 d . . .
H26A H 0.5804 0.9165 0.0130 0.061 Uiso 1 1 calc R . .
H26B H 0.6062 0.9760 -0.0748 0.061 Uiso 1 1 calc R . .
C262 C 0.7785(7) 0.9942(4) -0.0137(3) 0.0632(14) Uani 1 1 d . . .
H26C H 0.7400 1.0590 -0.0058 0.076 Uiso 1 1 calc R . .
H26D H 0.8206 0.9548 0.0333 0.076 Uiso 1 1 calc R . .
C263 C 0.9493(6) 0.9227(4) -0.0844(3) 0.0603(14) Uani 1 1 d . . .
H26E H 0.9911 0.8831 -0.0374 0.072 Uiso 1 1 calc R . .
H26F H 1.0300 0.9386 -0.1250 0.072 Uiso 1 1 calc R . .
C264 C 0.8339(5) 0.8588(4) -0.1049(2) 0.0502(11) Uani 1 1 d . . .
H26G H 0.7986 0.8949 -0.1545 0.060 Uiso 1 1 calc R . .
H26H H 0.8766 0.7929 -0.1085 0.060 Uiso 1 1 calc R . .
Cu3 Cu 0.97959(9) 0.81968(13) 0.34122(6) 0.0617(3) Uani 0.801(3) 1 d P A 1
Cl31 Cl 1.01536(18) 0.6680(2) 0.40041(11) 0.0590(5) Uani 0.801(3) 1 d P A 1
Cl32 Cl 0.9500(2) 0.9714(2) 0.28048(12) 0.0795(6) Uani 0.801(3) 1 d P A 1


_geom_special_details            
; 
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cu1 N13 1.963(3) . ?
Cu1 N23 1.975(3) . ?
Cu1 N21 2.153(3) . ?
Cu1 N11 2.236(3) . ?
Cu1 Cl11 2.2389(9) . ?
Cu2 Cl21 2.055(10) . ?
Cu2 Cl22 2.081(12) . ?
O11 C163 1.415(6) . ?
O11 C162 1.420(5) . ?
O21 C262 1.419(7) . ?
O21 C263 1.426(7) . ?
N11 C11 1.333(4) . ?
N11 N12 1.374(3) . ?
N12 C13 1.385(4) . ?
N12 C14 1.411(4) . ?
N13 C17 1.341(4) . ?
N13 C14 1.357(4) . ?
N14 C17 1.310(4) . ?
N14 C16 1.356(4) . ?
N15 C16 1.343(4) . ?
N15 C161 1.467(4) . ?
N15 C164 1.472(5) . ?
N21 C21 1.342(4) . ?
N21 N22 1.381(4) . ?
N22 C23 1.374(4) . ?
N22 C24 1.412(4) . ?
N23 C27 1.343(4) . ?
N23 C24 1.350(4) . ?
N24 C27 1.315(4) . ?
N24 C26 1.353(5) . ?
N25 C26 1.349(5) . ?
N25 C261 1.461(6) . ?
N25 C264 1.470(5) . ?
C11 C12 1.414(4) . ?
C11 C111 1.473(4) . ?
C12 C13 1.366(4) . ?
C12 H12 0.9500 . ?
C13 C131 1.480(4) . ?
C14 C15 1.364(4) . ?
C15 C16 1.419(4) . ?
C15 H15 0.9500 . ?
C17 H17 0.9500 . ?
C21 C22 1.411(5) . ?
C21 C211 1.470(5) . ?
C22 C23 1.369(5) . ?
C22 H22 0.9500 . ?
C23 C231 1.474(5) . ?
C24 C25 1.366(5) . ?
C25 C26 1.416(5) . ?
C25 H25 0.9500 . ?
C27 H27 0.9500 . ?
C111 C116 1.396(5) . ?
C111 C112 1.396(5) . ?
C112 C113 1.392(5) . ?
C112 H112 0.9500 . ?
C113 C114 1.388(6) . ?
C113 H113 0.9500 . ?
C114 C115 1.383(5) . ?
C114 H114 0.9500 . ?
C115 C116 1.388(5) . ?
C115 H115 0.9500 . ?
C116 H116 0.9500 . ?
C131 C132 1.384(5) . ?
C131 C136 1.391(5) . ?
C132 C133 1.395(5) . ?
C132 H132 0.9500 . ?
C133 C134 1.375(7) . ?
C133 H133 0.9500 . ?
C134 C135 1.381(6) . ?
C134 H134 0.9500 . ?
C135 C136 1.383(5) . ?
C135 H135 0.9500 . ?
C136 H136 0.9500 . ?
C161 C162 1.505(5) . ?
C161 H16A 0.9900 . ?
C161 H16B 0.9900 . ?
C162 H16C 0.9900 . ?
C162 H16D 0.9900 . ?
C163 C164 1.503(5) . ?
C163 H16E 0.9900 . ?
C163 H16F 0.9900 . ?
C164 H16G 0.9900 . ?
C164 H16H 0.9900 . ?
C211 C216 1.388(6) . ?
C211 C212 1.399(5) . ?
C212 C213 1.393(6) . ?
C212 H212 0.9500 . ?
C213 C214 1.371(7) . ?
C213 H213 0.9500 . ?
C214 C215 1.383(7) . ?
C214 H214 0.9500 . ?
C215 C216 1.391(5) . ?
C215 H215 0.9500 . ?
C216 H216 0.9500 . ?
C231 C236 1.392(5) . ?
C231 C232 1.396(5) . ?
C232 C233 1.391(6) . ?
C232 H232 0.9500 . ?
C233 C234 1.377(7) . ?
C233 H233 0.9500 . ?
C234 C235 1.388(7) . ?
C234 H234 0.9500 . ?
C235 C236 1.386(6) . ?
C235 H235 0.9500 . ?
C236 H236 0.9500 . ?
C261 C262 1.506(7) . ?
C261 H26A 0.9900 . ?
C261 H26B 0.9900 . ?
C262 H26C 0.9900 . ?
C262 H26D 0.9900 . ?
C263 C264 1.509(7) . ?
C263 H26E 0.9900 . ?
C263 H26F 0.9900 . ?
C264 H26G 0.9900 . ?
C264 H26H 0.9900 . ?
Cu3 Cl32 2.088(3) . ?
Cu3 Cl31 2.089(2) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N13 Cu1 N23 166.64(11) . . ?
N13 Cu1 N21 90.97(10) . . ?
N23 Cu1 N21 77.78(10) . . ?
N13 Cu1 N11 76.29(10) . . ?
N23 Cu1 N11 96.71(10) . . ?
N21 Cu1 N11 92.10(10) . . ?
N13 Cu1 Cl11 95.58(8) . . ?
N23 Cu1 Cl11 97.66(8) . . ?
N21 Cu1 Cl11 154.54(8) . . ?
N11 Cu1 Cl11 113.35(7) . . ?
Cl21 Cu2 Cl22 176.5(4) . . ?
C163 O11 C162 110.9(3) . . ?
C262 O21 C263 110.0(4) . . ?
C11 N11 N12 105.6(2) . . ?
C11 N11 Cu1 142.8(2) . . ?
N12 N11 Cu1 105.34(17) . . ?
N11 N12 C13 111.0(2) . . ?
N11 N12 C14 116.9(2) . . ?
C13 N12 C14 131.7(2) . . ?
C17 N13 C14 115.6(3) . . ?
C17 N13 Cu1 125.3(2) . . ?
C14 N13 Cu1 118.7(2) . . ?
C17 N14 C16 116.8(3) . . ?
C16 N15 C161 124.2(3) . . ?
C16 N15 C164 121.7(3) . . ?
C161 N15 C164 112.2(3) . . ?
C21 N21 N22 105.2(3) . . ?
C21 N21 Cu1 138.6(2) . . ?
N22 N21 Cu1 103.15(18) . . ?
C23 N22 N21 111.4(3) . . ?
C23 N22 C24 132.9(3) . . ?
N21 N22 C24 115.4(2) . . ?
C27 N23 C24 115.1(3) . . ?
C27 N23 Cu1 129.5(2) . . ?
C24 N23 Cu1 115.1(2) . . ?
C27 N24 C26 117.1(3) . . ?
C26 N25 C261 124.2(4) . . ?
C26 N25 C264 122.5(4) . . ?
C261 N25 C264 113.2(3) . . ?
N11 C11 C12 110.7(3) . . ?
N11 C11 C111 120.8(3) . . ?
C12 C11 C111 128.5(3) . . ?
C13 C12 C11 106.5(3) . . ?
C13 C12 H12 126.7 . . ?
C11 C12 H12 126.7 . . ?
C12 C13 N12 106.2(3) . . ?
C12 C13 C131 131.1(3) . . ?
N12 C13 C131 122.6(3) . . ?
N13 C14 C15 122.1(3) . . ?
N13 C14 N12 113.9(3) . . ?
C15 C14 N12 124.0(3) . . ?
C14 C15 C16 117.2(3) . . ?
C14 C15 H15 121.4 . . ?
C16 C15 H15 121.4 . . ?
N15 C16 N14 117.4(3) . . ?
N15 C16 C15 122.6(3) . . ?
N14 C16 C15 120.1(3) . . ?
N14 C17 N13 127.3(3) . . ?
N14 C17 H17 116.3 . . ?
N13 C17 H17 116.3 . . ?
N21 C21 C22 110.3(3) . . ?
N21 C21 C211 122.8(3) . . ?
C22 C21 C211 126.9(3) . . ?
C23 C22 C21 107.0(3) . . ?
C23 C22 H22 126.5 . . ?
C21 C22 H22 126.5 . . ?
C22 C23 N22 106.1(3) . . ?
C22 C23 C231 127.9(3) . . ?
N22 C23 C231 125.8(3) . . ?
N23 C24 C25 123.6(3) . . ?
N23 C24 N22 113.7(3) . . ?
C25 C24 N22 122.6(3) . . ?
C24 C25 C26 116.1(3) . . ?
C24 C25 H25 121.9 . . ?
C26 C25 H25 121.9 . . ?
N25 C26 N24 117.4(3) . . ?
N25 C26 C25 122.0(4) . . ?
N24 C26 C25 120.6(3) . . ?
N24 C27 N23 127.0(3) . . ?
N24 C27 H27 116.5 . . ?
N23 C27 H27 116.5 . . ?
C116 C111 C112 119.2(3) . . ?
C116 C111 C11 120.8(3) . . ?
C112 C111 C11 119.9(3) . . ?
C113 C112 C111 120.3(3) . . ?
C113 C112 H112 119.8 . . ?
C111 C112 H112 119.8 . . ?
C114 C113 C112 119.8(3) . . ?
C114 C113 H113 120.1 . . ?
C112 C113 H113 120.1 . . ?
C115 C114 C113 120.1(3) . . ?
C115 C114 H114 120.0 . . ?
C113 C114 H114 120.0 . . ?
C114 C115 C116 120.3(3) . . ?
C114 C115 H115 119.8 . . ?
C116 C115 H115 119.8 . . ?
C115 C116 C111 120.1(3) . . ?
C115 C116 H116 119.9 . . ?
C111 C116 H116 119.9 . . ?
C132 C131 C136 119.7(3) . . ?
C132 C131 C13 121.2(3) . . ?
C136 C131 C13 119.1(3) . . ?
C131 C132 C133 119.4(4) . . ?
C131 C132 H132 120.3 . . ?
C133 C132 H132 120.3 . . ?
C134 C133 C132 120.4(4) . . ?
C134 C133 H133 119.8 . . ?
C132 C133 H133 119.8 . . ?
C133 C134 C135 120.4(3) . . ?
C133 C134 H134 119.8 . . ?
C135 C134 H134 119.8 . . ?
C134 C135 C136 119.6(4) . . ?
C134 C135 H135 120.2 . . ?
C136 C135 H135 120.2 . . ?
C135 C136 C131 120.4(3) . . ?
C135 C136 H136 119.8 . . ?
C131 C136 H136 119.8 . . ?
N15 C161 C162 110.1(3) . . ?
N15 C161 H16A 109.6 . . ?
C162 C161 H16A 109.6 . . ?
N15 C161 H16B 109.6 . . ?
C162 C161 H16B 109.6 . . ?
H16A C161 H16B 108.1 . . ?
O11 C162 C161 112.1(3) . . ?
O11 C162 H16C 109.2 . . ?
C161 C162 H16C 109.2 . . ?
O11 C162 H16D 109.2 . . ?
C161 C162 H16D 109.2 . . ?
H16C C162 H16D 107.9 . . ?
O11 C163 C164 111.7(3) . . ?
O11 C163 H16E 109.3 . . ?
C164 C163 H16E 109.3 . . ?
O11 C163 H16F 109.3 . . ?
C164 C163 H16F 109.3 . . ?
H16E C163 H16F 107.9 . . ?
N15 C164 C163 108.8(3) . . ?
N15 C164 H16G 109.9 . . ?
C163 C164 H16G 109.9 . . ?
N15 C164 H16H 109.9 . . ?
C163 C164 H16H 109.9 . . ?
H16G C164 H16H 108.3 . . ?
C216 C211 C212 119.2(3) . . ?
C216 C211 C21 121.3(3) . . ?
C212 C211 C21 119.4(3) . . ?
C213 C212 C211 119.8(4) . . ?
C213 C212 H212 120.1 . . ?
C211 C212 H212 120.1 . . ?
C214 C213 C212 120.6(4) . . ?
C214 C213 H213 119.7 . . ?
C212 C213 H213 119.7 . . ?
C213 C214 C215 120.0(4) . . ?
C213 C214 H214 120.0 . . ?
C215 C214 H214 120.0 . . ?
C214 C215 C216 120.2(5) . . ?
C214 C215 H215 119.9 . . ?
C216 C215 H215 119.9 . . ?
C211 C216 C215 120.2(4) . . ?
C211 C216 H216 119.9 . . ?
C215 C216 H216 119.9 . . ?
C236 C231 C232 119.0(3) . . ?
C236 C231 C23 121.1(3) . . ?
C232 C231 C23 119.7(3) . . ?
C233 C232 C231 119.7(4) . . ?
C233 C232 H232 120.1 . . ?
C231 C232 H232 120.1 . . ?
C234 C233 C232 120.9(4) . . ?
C234 C233 H233 119.6 . . ?
C232 C233 H233 119.6 . . ?
C233 C234 C235 119.8(4) . . ?
C233 C234 H234 120.1 . . ?
C235 C234 H234 120.1 . . ?
C236 C235 C234 119.8(4) . . ?
C236 C235 H235 120.1 . . ?
C234 C235 H235 120.1 . . ?
C235 C236 C231 120.8(4) . . ?
C235 C236 H236 119.6 . . ?
C231 C236 H236 119.6 . . ?
N25 C261 C262 110.3(4) . . ?
N25 C261 H26A 109.6 . . ?
C262 C261 H26A 109.6 . . ?
N25 C261 H26B 109.6 . . ?
C262 C261 H26B 109.6 . . ?
H26A C261 H26B 108.1 . . ?
O21 C262 C261 110.7(4) . . ?
O21 C262 H26C 109.5 . . ?
C261 C262 H26C 109.5 . . ?
O21 C262 H26D 109.5 . . ?
C261 C262 H26D 109.5 . . ?
H26C C262 H26D 108.1 . . ?
O21 C263 C264 111.9(4) . . ?
O21 C263 H26E 109.2 . . ?
C264 C263 H26E 109.2 . . ?
O21 C263 H26F 109.2 . . ?
C264 C263 H26F 109.2 . . ?
H26E C263 H26F 107.9 . . ?
N25 C264 C263 108.9(4) . . ?
N25 C264 H26G 109.9 . . ?
C263 C264 H26G 109.9 . . ?
N25 C264 H26H 109.9 . . ?
C263 C264 H26H 109.9 . . ?
H26G C264 H26H 108.3 . . ?
Cl32 Cu3 Cl31 178.32(9) . . ?

_diffrn_measured_fraction_theta_max 0.990
_diffrn_reflns_theta_full        25.50
_diffrn_measured_fraction_theta_full 0.991
_refine_diff_density_max         0.902
_refine_diff_density_min         -0.798
_refine_diff_density_rms         0.064
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_mbb_037
_database_code_depnum_ccdc_archive 'CCDC 1424213'
_audit_update_record             
;
2015-09-14 deposited with the CCDC.
2015-11-09 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         'C25 H18 N4 O'
_chemical_formula_sum            'C25 H18 N4 O'
_chemical_melting_point          ?

_exptl_crystal_description       prism
_exptl_crystal_colour            colorless

_diffrn_ambient_temperature      150(2)
_chemical_formula_weight         390.43

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   'P b c a'
_symmetry_int_tables_number      61
_chemical_absolute_configuration ?
_symmetry_space_group_name_Hall  '-P 2ac 2ab'


loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'-x-1/2, y-1/2, z'
'x, -y-1/2, z-1/2'

_cell_length_a                   7.9801(7)
_cell_length_b                   18.5685(19)
_cell_length_c                   26.854(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     3979.1(7)
_cell_formula_units_Z            8
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    3349
_cell_measurement_theta_min      2.32
_cell_measurement_theta_max      25.41
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.05
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.303
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1632
_exptl_absorpt_coefficient_mu    0.082

_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9639
_exptl_absorpt_correction_T_max  0.9959
_exptl_absorpt_process_details   'SADABS (Bruker, 2004)'

_exptl_special_details           
; 
 ? 
;

_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker Nonius X8Apex CCD area-detector'
_diffrn_measurement_method       'φ scans'
_diffrn_detector_area_resol_mean 25
_diffrn_standards_number         0
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        0
_diffrn_reflns_number            22263
_diffrn_reflns_av_R_equivalents  0.0666
_diffrn_reflns_av_sigmaI/netI    0.0504
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_l_min       -33
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_theta_min         2.19
_diffrn_reflns_theta_max         26.02
_reflns_number_total             3912
_reflns_number_gt                2744
_reflns_threshold_expression     >2σ(I)


_computing_data_collection       'APEX2 (Bruker, 2004)'
_computing_cell_refinement       'SAINT (Bruker, 2004)'
_computing_data_reduction        'SAINT (Bruker, 2004)'
_computing_structure_solution    'SHELXTL (Bruker, 2004)'
_computing_structure_refinement  'SHELXTL (Bruker, 2004)'
_computing_molecular_graphics    'SHELXTL (Bruker, 2004)'
_computing_publication_material  'SHELXTL (Bruker, 2004)'

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0455P)²+0.2135P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.0035(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         3912
_refine_ls_number_parameters     272
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0713
_refine_ls_R_factor_gt           0.0403
_refine_ls_wR_factor_ref         0.0946
_refine_ls_wR_factor_gt          0.0862
_refine_ls_goodness_of_fit_ref   1.008
_refine_ls_restrained_S_all      1.008
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O11 O 0.44577(14) 0.12176(6) 0.59719(4) 0.0274(3) Uani 1 1 d . . .
N11 N 0.48513(16) 0.11068(6) 0.78277(5) 0.0196(3) Uani 1 1 d . . .
N12 N 0.54332(15) 0.17693(6) 0.76786(4) 0.0169(3) Uani 1 1 d . . .
N13 N 0.67453(15) 0.24129(7) 0.70433(5) 0.0194(3) Uani 1 1 d . . .
N14 N 0.62615(15) 0.21415(7) 0.61840(4) 0.0201(3) Uani 1 1 d . . .
C11 C 0.49497(18) 0.11252(8) 0.83226(5) 0.0175(3) Uani 1 1 d . . .
C12 C 0.55998(18) 0.17878(8) 0.84911(6) 0.0184(3) Uani 1 1 d . . .
H12 H 0.5808 0.1922 0.8827 0.022 Uiso 1 1 calc R . .
C13 C 0.58723(17) 0.21995(8) 0.80785(5) 0.0166(3) Uani 1 1 d . . .
C14 C 0.56815(18) 0.18828(8) 0.71639(5) 0.0169(3) Uani 1 1 d . . .
C15 C 0.48743(19) 0.14576(8) 0.68184(6) 0.0192(3) Uani 1 1 d . . .
H15 H 0.4127 0.1083 0.6911 0.023 Uiso 1 1 calc R . .
C16 C 0.52336(19) 0.16176(8) 0.63268(6) 0.0203(4) Uani 1 1 d . . .
C17 C 0.69554(19) 0.25118(8) 0.65585(6) 0.0207(4) Uani 1 1 d . . .
H17 H 0.7688 0.2892 0.6466 0.025 Uiso 1 1 calc R . .
C111 C 0.43834(19) 0.05102(8) 0.86271(6) 0.0186(3) Uani 1 1 d . . .
C112 C 0.3025(2) 0.00912(8) 0.84784(6) 0.0223(4) Uani 1 1 d . . .
H112 H 0.2464 0.0196 0.8175 0.027 Uiso 1 1 calc R . .
C113 C 0.2489(2) -0.04784(9) 0.87725(6) 0.0274(4) Uani 1 1 d . . .
H113 H 0.1548 -0.0757 0.8673 0.033 Uiso 1 1 calc R . .
C114 C 0.3321(2) -0.06415(9) 0.92110(6) 0.0283(4) Uani 1 1 d . . .
H114 H 0.2958 -0.1034 0.9410 0.034 Uiso 1 1 calc R . .
C115 C 0.4677(2) -0.02335(8) 0.93578(6) 0.0265(4) Uani 1 1 d . . .
H115 H 0.5255 -0.0351 0.9656 0.032 Uiso 1 1 calc R . .
C116 C 0.5203(2) 0.03476(8) 0.90723(6) 0.0230(4) Uani 1 1 d . . .
H116 H 0.6120 0.0634 0.9180 0.028 Uiso 1 1 calc R . .
C131 C 0.63266(18) 0.29710(8) 0.80547(5) 0.0166(3) Uani 1 1 d . . .
C132 C 0.53669(19) 0.34665(8) 0.77867(6) 0.0207(4) Uani 1 1 d . . .
H132 H 0.4416 0.3309 0.7604 0.025 Uiso 1 1 calc R . .
C133 C 0.5805(2) 0.41899(8) 0.77876(6) 0.0247(4) Uani 1 1 d . . .
H133 H 0.5160 0.4526 0.7602 0.030 Uiso 1 1 calc R . .
C134 C 0.7178(2) 0.44243(8) 0.80581(6) 0.0264(4) Uani 1 1 d . . .
H134 H 0.7479 0.4919 0.8054 0.032 Uiso 1 1 calc R . .
C135 C 0.8110(2) 0.39407(8) 0.83333(6) 0.0249(4) Uani 1 1 d . . .
H135 H 0.9042 0.4103 0.8523 0.030 Uiso 1 1 calc R . .
C136 C 0.76840(19) 0.32164(8) 0.83325(6) 0.0209(4) Uani 1 1 d . . .
H136 H 0.8324 0.2885 0.8523 0.025 Uiso 1 1 calc R . .
C161 C 0.4737(2) 0.14079(8) 0.54686(6) 0.0218(4) Uani 1 1 d . . .
C162 C 0.5763(2) 0.09736(9) 0.51869(6) 0.0309(4) Uani 1 1 d . . .
H162 H 0.6311 0.0571 0.5332 0.037 Uiso 1 1 calc R . .
C163 C 0.5980(2) 0.11365(10) 0.46882(6) 0.0345(4) Uani 1 1 d . . .
H163 H 0.6687 0.0844 0.4488 0.041 Uiso 1 1 calc R . .
C164 C 0.5178(2) 0.17190(9) 0.44798(6) 0.0302(4) Uani 1 1 d . . .
H164 H 0.5336 0.1828 0.4137 0.036 Uiso 1 1 calc R . .
C165 C 0.4144(2) 0.21466(9) 0.47676(6) 0.0315(4) Uani 1 1 d . . .
H165 H 0.3592 0.2549 0.4623 0.038 Uiso 1 1 calc R . .
C166 C 0.3913(2) 0.19890(9) 0.52661(6) 0.0285(4) Uani 1 1 d . . .
H166 H 0.3197 0.2278 0.5466 0.034 Uiso 1 1 calc R . .


_geom_special_details            
; 
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O11 C16 1.3577(18) . ?
O11 C161 1.4145(18) . ?
N11 C11 1.3317(19) . ?
N11 N12 1.3745(16) . ?
N12 C13 1.3836(19) . ?
N12 C14 1.4122(19) . ?
N13 C17 1.3253(19) . ?
N13 C14 1.3396(19) . ?
N14 C16 1.3291(19) . ?
N14 C17 1.3382(19) . ?
C11 C12 1.410(2) . ?
C11 C111 1.475(2) . ?
C12 C13 1.364(2) . ?
C12 H12 0.9500 . ?
C13 C131 1.4791(19) . ?
C14 C15 1.378(2) . ?
C15 C16 1.383(2) . ?
C15 H15 0.9500 . ?
C17 H17 0.9500 . ?
C111 C112 1.393(2) . ?
C111 C116 1.396(2) . ?
C112 C113 1.388(2) . ?
C112 H112 0.9500 . ?
C113 C114 1.386(2) . ?
C113 H113 0.9500 . ?
C114 C115 1.378(2) . ?
C114 H114 0.9500 . ?
C115 C116 1.389(2) . ?
C115 H115 0.9500 . ?
C116 H116 0.9500 . ?
C131 C136 1.392(2) . ?
C131 C132 1.397(2) . ?
C132 C133 1.388(2) . ?
C132 H132 0.9500 . ?
C133 C134 1.385(2) . ?
C133 H133 0.9500 . ?
C134 C135 1.381(2) . ?
C134 H134 0.9500 . ?
C135 C136 1.387(2) . ?
C135 H135 0.9500 . ?
C136 H136 0.9500 . ?
C161 C166 1.376(2) . ?
C161 C162 1.376(2) . ?
C162 C163 1.384(2) . ?
C162 H162 0.9500 . ?
C163 C164 1.375(2) . ?
C163 H163 0.9500 . ?
C164 C165 1.381(2) . ?
C164 H164 0.9500 . ?
C165 C166 1.382(2) . ?
C165 H165 0.9500 . ?
C166 H166 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C16 O11 C161 117.53(12) . . ?
C11 N11 N12 104.35(11) . . ?
N11 N12 C13 112.10(11) . . ?
N11 N12 C14 117.79(12) . . ?
C13 N12 C14 129.64(12) . . ?
C17 N13 C14 114.80(13) . . ?
C16 N14 C17 114.50(13) . . ?
N11 C11 C12 111.37(13) . . ?
N11 C11 C111 121.01(13) . . ?
C12 C11 C111 127.61(14) . . ?
C13 C12 C11 106.69(13) . . ?
C13 C12 H12 126.7 . . ?
C11 C12 H12 126.7 . . ?
C12 C13 N12 105.46(13) . . ?
C12 C13 C131 128.11(13) . . ?
N12 C13 C131 126.00(13) . . ?
N13 C14 C15 123.68(14) . . ?
N13 C14 N12 115.80(13) . . ?
C15 C14 N12 120.52(13) . . ?
C14 C15 C16 115.00(14) . . ?
C14 C15 H15 122.5 . . ?
C16 C15 H15 122.5 . . ?
N14 C16 O11 118.65(13) . . ?
N14 C16 C15 124.09(14) . . ?
O11 C16 C15 117.26(14) . . ?
N13 C17 N14 127.93(14) . . ?
N13 C17 H17 116.0 . . ?
N14 C17 H17 116.0 . . ?
C112 C111 C116 119.30(14) . . ?
C112 C111 C11 120.79(14) . . ?
C116 C111 C11 119.91(14) . . ?
C113 C112 C111 120.18(15) . . ?
C113 C112 H112 119.9 . . ?
C111 C112 H112 119.9 . . ?
C114 C113 C112 120.16(15) . . ?
C114 C113 H113 119.9 . . ?
C112 C113 H113 119.9 . . ?
C115 C114 C113 119.94(15) . . ?
C115 C114 H114 120.0 . . ?
C113 C114 H114 120.0 . . ?
C114 C115 C116 120.44(16) . . ?
C114 C115 H115 119.8 . . ?
C116 C115 H115 119.8 . . ?
C115 C116 C111 119.95(15) . . ?
C115 C116 H116 120.0 . . ?
C111 C116 H116 120.0 . . ?
C136 C131 C132 119.15(14) . . ?
C136 C131 C13 118.99(13) . . ?
C132 C131 C13 121.73(13) . . ?
C133 C132 C131 119.90(14) . . ?
C133 C132 H132 120.1 . . ?
C131 C132 H132 120.1 . . ?
C134 C133 C132 120.29(15) . . ?
C134 C133 H133 119.9 . . ?
C132 C133 H133 119.9 . . ?
C135 C134 C133 120.18(15) . . ?
C135 C134 H134 119.9 . . ?
C133 C134 H134 119.9 . . ?
C134 C135 C136 119.83(15) . . ?
C134 C135 H135 120.1 . . ?
C136 C135 H135 120.1 . . ?
C135 C136 C131 120.61(15) . . ?
C135 C136 H136 119.7 . . ?
C131 C136 H136 119.7 . . ?
C166 C161 C162 121.78(15) . . ?
C166 C161 O11 119.90(14) . . ?
C162 C161 O11 118.21(14) . . ?
C161 C162 C163 118.59(16) . . ?
C161 C162 H162 120.7 . . ?
C163 C162 H162 120.7 . . ?
C164 C163 C162 120.49(16) . . ?
C164 C163 H163 119.8 . . ?
C162 C163 H163 119.8 . . ?
C163 C164 C165 120.13(16) . . ?
C163 C164 H164 119.9 . . ?
C165 C164 H164 119.9 . . ?
C164 C165 C166 119.97(16) . . ?
C164 C165 H165 120.0 . . ?
C166 C165 H165 120.0 . . ?
C161 C166 C165 119.03(15) . . ?
C161 C166 H166 120.5 . . ?
C165 C166 H166 120.5 . . ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        25.50
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.266
_refine_diff_density_min         -0.176
_refine_diff_density_rms         0.047
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_mbb_063
_database_code_depnum_ccdc_archive 'CCDC 1424214'
_audit_update_record             
;
2015-09-14 deposited with the CCDC.
2015-11-09 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         '2(C46 H42 Br Cu N10 O2), (Br4 Cu2)'
_chemical_formula_sum            'C92 H84 Br6 Cu4 N20 O4'
_chemical_melting_point          ?

_exptl_crystal_description       prism
_exptl_crystal_colour            yellow

_diffrn_ambient_temperature      150(2)
_chemical_formula_weight         2267.41

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'C 2/c'
_symmetry_int_tables_number      15
_chemical_absolute_configuration ?
_symmetry_space_group_name_Hall  '-C 2yc'

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   20.0008(5)
_cell_length_b                   18.3973(4)
_cell_length_c                   24.6565(7)
_cell_angle_alpha                90.00
_cell_angle_beta                 95.0920(10)
_cell_angle_gamma                90.00
_cell_volume                     9036.8(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.667
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             4536
_exptl_absorpt_coefficient_mu    3.645

_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.2908
_exptl_absorpt_correction_T_max  0.7119
_exptl_absorpt_process_details   'SADABS (Bruker, 2004)'

_exptl_special_details           
; 
 ? 
;


_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker Nonius X8Apex CCD area-detector'
_diffrn_measurement_method       'φ scans'
_diffrn_detector_area_resol_mean 25
_diffrn_standards_number         0
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        0
_diffrn_reflns_number            27137
_diffrn_reflns_av_R_equivalents  0.0308
_diffrn_reflns_av_sigmaI/netI    0.0384
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_theta_min         1.66
_diffrn_reflns_theta_max         26.37
_reflns_number_total             9228
_reflns_number_gt                7124
_reflns_threshold_expression     >2σ(I)


_computing_data_collection       'APEX2 (Bruker, 2004)'
_computing_cell_refinement       'SAINT (Bruker, 2004)'
_computing_data_reduction        'SAINT (Bruker, 2004)'
_computing_structure_solution    'SHELXTL (Bruker, 2004)'
_computing_structure_refinement  'SHELXTL (Bruker, 2004)'
_computing_molecular_graphics    'SHELXTL (Bruker, 2004)'
_computing_publication_material  'SHELXTL (Bruker, 2004)'

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0356P)²+3.0217P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         9228
_refine_ls_number_parameters     570
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0524
_refine_ls_R_factor_gt           0.0314
_refine_ls_wR_factor_ref         0.0743
_refine_ls_wR_factor_gt          0.0693
_refine_ls_goodness_of_fit_ref   1.050
_refine_ls_restrained_S_all      1.050
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Br1 Br 0.114771(14) 0.043176(13) 0.503699(11) 0.02405(8) Uani 1 1 d . . .
Br2 Br 0.0000 -0.26579(2) 0.2500 0.03550(11) Uani 1 2 d S . .
Br3 Br 0.0000 -0.66959(2) 0.2500 0.04250(13) Uani 1 2 d S . .
Br4 Br 0.099646(15) -0.467369(16) 0.256671(13) 0.03421(9) Uani 1 1 d . . .
Cu1 Cu 0.049530(15) 0.004337(15) 0.420497(12) 0.01536(8) Uani 1 1 d . . .
Cu2 Cu 0.0000 -0.39159(3) 0.2500 0.03429(13) Uani 1 2 d S . .
Cu3 Cu 0.0000 -0.54352(3) 0.2500 0.03623(14) Uani 1 2 d S . .
O11 O 0.21153(9) -0.44069(9) 0.39976(8) 0.0278(5) Uani 1 1 d . . .
O21 O -0.11474(11) 0.45054(10) 0.41299(9) 0.0391(5) Uani 1 1 d . . .
N11 N -0.02516(10) -0.05205(10) 0.37350(8) 0.0170(5) Uani 1 1 d . . .
N12 N -0.02155(10) -0.12347(10) 0.39053(8) 0.0159(5) Uani 1 1 d . . .
N13 N 0.08440(10) -0.09524(10) 0.42732(8) 0.0156(5) Uani 1 1 d . . .
N14 N 0.17285(10) -0.18189(11) 0.43947(9) 0.0197(5) Uani 1 1 d . . .
N15 N 0.15576(11) -0.30234(11) 0.41584(9) 0.0213(5) Uani 1 1 d . . .
N21 N 0.10730(11) 0.05730(10) 0.35759(8) 0.0169(5) Uani 1 1 d . . .
N22 N 0.10615(10) 0.13004(10) 0.37077(8) 0.0156(5) Uani 1 1 d . . .
N23 N 0.01126(10) 0.10269(10) 0.41442(8) 0.0167(5) Uani 1 1 d . . .
N24 N -0.06724(11) 0.19115(11) 0.43872(9) 0.0216(5) Uani 1 1 d . . .
N25 N -0.05268(12) 0.31284(11) 0.42091(10) 0.0259(5) Uani 1 1 d . . .
C11 C -0.08660(13) -0.04465(13) 0.34807(10) 0.0168(5) Uani 1 1 d . . .
C12 C -0.12255(13) -0.11051(13) 0.35000(10) 0.0184(6) Uani 1 1 d . . .
H12 H -0.1673 -0.1191 0.3351 0.022 Uiso 1 1 calc R . .
C13 C -0.08074(12) -0.15944(13) 0.37736(10) 0.0164(5) Uani 1 1 d . . .
C14 C 0.04293(12) -0.14885(13) 0.40826(10) 0.0153(5) Uani 1 1 d . . .
C15 C 0.06247(13) -0.21903(13) 0.40299(10) 0.0178(6) Uani 1 1 d . . .
H15 H 0.0321 -0.2555 0.3889 0.021 Uiso 1 1 calc R . .
C16 C 0.13030(13) -0.23488(13) 0.41953(10) 0.0178(6) Uani 1 1 d . . .
C17 C 0.14817(13) -0.11562(13) 0.44151(10) 0.0197(6) Uani 1 1 d . . .
H17 H 0.1785 -0.0784 0.4543 0.024 Uiso 1 1 calc R . .
C21 C 0.16721(13) 0.04584(13) 0.33956(10) 0.0173(5) Uani 1 1 d . . .
C22 C 0.20542(13) 0.11051(13) 0.34287(11) 0.0200(6) Uani 1 1 d . . .
H22 H 0.2501 0.1162 0.3332 0.024 Uiso 1 1 calc R . .
C23 C 0.16630(13) 0.16319(13) 0.36249(10) 0.0171(5) Uani 1 1 d . . .
C24 C 0.04784(12) 0.15567(13) 0.39318(10) 0.0156(5) Uani 1 1 d . . .
C25 C 0.02888(13) 0.22658(13) 0.39266(10) 0.0197(6) Uani 1 1 d . . .
H25 H 0.0542 0.2628 0.3762 0.024 Uiso 1 1 calc R . .
C26 C -0.02982(13) 0.24425(13) 0.41739(10) 0.0201(6) Uani 1 1 d . . .
C27 C -0.04493(13) 0.12443(13) 0.43534(10) 0.0198(6) Uani 1 1 d . . .
H27 H -0.0716 0.0873 0.4493 0.024 Uiso 1 1 calc R . .
C111 C -0.10943(13) 0.02485(13) 0.32345(10) 0.0180(6) Uani 1 1 d . . .
C112 C -0.17734(14) 0.04263(14) 0.31968(11) 0.0225(6) Uani 1 1 d . . .
H112 H -0.2089 0.0088 0.3314 0.027 Uiso 1 1 calc R . .
C113 C -0.19909(15) 0.10908(15) 0.29905(11) 0.0291(7) Uani 1 1 d . . .
H113 H -0.2455 0.1207 0.2964 0.035 Uiso 1 1 calc R . .
C114 C -0.15335(16) 0.15883(15) 0.28219(11) 0.0312(7) Uani 1 1 d . . .
H114 H -0.1682 0.2054 0.2696 0.037 Uiso 1 1 calc R . .
C115 C -0.08603(15) 0.14099(15) 0.28363(11) 0.0279(7) Uani 1 1 d . . .
H115 H -0.0549 0.1747 0.2710 0.033 Uiso 1 1 calc R . .
C116 C -0.06393(13) 0.07349(14) 0.30366(10) 0.0219(6) Uani 1 1 d . . .
H116 H -0.0179 0.0606 0.3038 0.026 Uiso 1 1 calc R . .
C131 C -0.09235(12) -0.23368(13) 0.39766(11) 0.0180(6) Uani 1 1 d . . .
C132 C -0.10566(13) -0.29208(14) 0.36244(12) 0.0236(6) Uani 1 1 d . . .
H132 H -0.1087 -0.2848 0.3242 0.028 Uiso 1 1 calc R . .
C133 C -0.11443(14) -0.36123(15) 0.38365(13) 0.0309(7) Uani 1 1 d . . .
H133 H -0.1223 -0.4015 0.3598 0.037 Uiso 1 1 calc R . .
C134 C -0.11176(14) -0.37149(15) 0.43923(13) 0.0336(7) Uani 1 1 d . . .
H134 H -0.1182 -0.4187 0.4535 0.040 Uiso 1 1 calc R . .
C135 C -0.09973(14) -0.31363(14) 0.47422(13) 0.0295(7) Uani 1 1 d . . .
H135 H -0.0985 -0.3210 0.5124 0.035 Uiso 1 1 calc R . .
C136 C -0.08945(13) -0.24501(14) 0.45387(11) 0.0216(6) Uani 1 1 d . . .
H136 H -0.0804 -0.2054 0.4781 0.026 Uiso 1 1 calc R . .
C161 C 0.11570(14) -0.36015(13) 0.38708(12) 0.0266(7) Uani 1 1 d . . .
H16A H 0.1181 -0.3550 0.3473 0.032 Uiso 1 1 calc R . .
H16B H 0.0681 -0.3555 0.3947 0.032 Uiso 1 1 calc R . .
C162 C 0.14209(14) -0.43403(14) 0.40547(12) 0.0265(6) Uani 1 1 d . . .
H16C H 0.1339 -0.4415 0.4441 0.032 Uiso 1 1 calc R . .
H16D H 0.1174 -0.4722 0.3836 0.032 Uiso 1 1 calc R . .
C163 C 0.24771(14) -0.38968(14) 0.43401(12) 0.0289(7) Uani 1 1 d . . .
H16E H 0.2964 -0.3967 0.4315 0.035 Uiso 1 1 calc R . .
H16F H 0.2384 -0.3985 0.4722 0.035 Uiso 1 1 calc R . .
C164 C 0.22902(13) -0.31233(14) 0.41864(12) 0.0261(6) Uani 1 1 d . . .
H16G H 0.2510 -0.2786 0.4460 0.031 Uiso 1 1 calc R . .
H16H H 0.2452 -0.3007 0.3829 0.031 Uiso 1 1 calc R . .
C211 C 0.18492(13) -0.02589(13) 0.31816(10) 0.0180(6) Uani 1 1 d . . .
C212 C 0.25072(14) -0.04101(14) 0.30771(11) 0.0253(6) Uani 1 1 d . . .
H212 H 0.2846 -0.0053 0.3152 0.030 Uiso 1 1 calc R . .
C213 C 0.26724(15) -0.10791(15) 0.28646(12) 0.0298(7) Uani 1 1 d . . .
H213 H 0.3121 -0.1176 0.2789 0.036 Uiso 1 1 calc R . .
C214 C 0.21826(15) -0.16031(15) 0.27635(11) 0.0301(7) Uani 1 1 d . . .
H214 H 0.2298 -0.2063 0.2624 0.036 Uiso 1 1 calc R . .
C215 C 0.15260(15) -0.14629(14) 0.28644(11) 0.0266(6) Uani 1 1 d . . .
H215 H 0.1192 -0.1826 0.2797 0.032 Uiso 1 1 calc R . .
C216 C 0.13579(14) -0.07885(14) 0.30649(10) 0.0217(6) Uani 1 1 d . . .
H216 H 0.0904 -0.0686 0.3123 0.026 Uiso 1 1 calc R . .
C231 C 0.18388(12) 0.23979(13) 0.37545(10) 0.0174(6) Uani 1 1 d . . .
C232 C 0.22726(13) 0.25430(14) 0.42128(11) 0.0232(6) Uani 1 1 d . . .
H232 H 0.2447 0.2155 0.4437 0.028 Uiso 1 1 calc R . .
C233 C 0.24523(14) 0.32542(14) 0.43436(12) 0.0287(7) Uani 1 1 d . . .
H233 H 0.2749 0.3350 0.4658 0.034 Uiso 1 1 calc R . .
C234 C 0.22042(14) 0.38219(14) 0.40220(12) 0.0281(7) Uani 1 1 d . . .
H234 H 0.2321 0.4308 0.4119 0.034 Uiso 1 1 calc R . .
C235 C 0.17846(14) 0.36808(14) 0.35573(12) 0.0281(7) Uani 1 1 d . . .
H235 H 0.1620 0.4071 0.3331 0.034 Uiso 1 1 calc R . .
C236 C 0.16040(14) 0.29732(14) 0.34204(11) 0.0229(6) Uani 1 1 d . . .
H236 H 0.1320 0.2879 0.3099 0.027 Uiso 1 1 calc R . .
C261 C -0.01579(15) 0.37719(14) 0.40443(13) 0.0344(8) Uani 1 1 d . . .
H26A H 0.0159 0.3629 0.3777 0.041 Uiso 1 1 calc R . .
H26B H 0.0104 0.3982 0.4366 0.041 Uiso 1 1 calc R . .
C262 C -0.06357(16) 0.43222(16) 0.37981(14) 0.0395(8) Uani 1 1 d . . .
H26C H -0.0383 0.4768 0.3721 0.047 Uiso 1 1 calc R . .
H26D H -0.0843 0.4133 0.3447 0.047 Uiso 1 1 calc R . .
C263 C -0.15125(16) 0.38772(16) 0.42531(14) 0.0407(8) Uani 1 1 d . . .
H26E H -0.1733 0.3673 0.3911 0.049 Uiso 1 1 calc R . .
H26F H -0.1869 0.4016 0.4487 0.049 Uiso 1 1 calc R . .
C264 C -0.10804(16) 0.33079(15) 0.45356(13) 0.0371(8) Uani 1 1 d . . .
H26G H -0.0899 0.3487 0.4898 0.045 Uiso 1 1 calc R . .
H26H H -0.1351 0.2867 0.4589 0.045 Uiso 1 1 calc R . .


_geom_special_details            
; 
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Br1 Cu1 2.4386(4) . ?
Br2 Cu2 2.3143(7) . ?
Br3 Cu3 2.3192(6) . ?
Br4 Cu2 2.4258(4) . ?
Br4 Cu3 2.4298(4) . ?
Cu1 N13 1.9621(19) . ?
Cu1 N23 1.965(2) . ?
Cu1 N11 2.084(2) . ?
Cu1 N21 2.238(2) . ?
Cu2 Br4 2.4258(4) 2 ?
Cu2 Cu3 2.7952(7) . ?
Cu3 Br4 2.4298(4) 2 ?
O11 C162 1.414(3) . ?
O11 C163 1.417(3) . ?
O21 C262 1.407(3) . ?
O21 C263 1.414(4) . ?
N11 C11 1.336(3) . ?
N11 N12 1.379(3) . ?
N12 C13 1.370(3) . ?
N12 C14 1.404(3) . ?
N13 C17 1.346(3) . ?
N13 C14 1.346(3) . ?
N14 C17 1.318(3) . ?
N14 C16 1.357(3) . ?
N15 C16 1.348(3) . ?
N15 C164 1.472(3) . ?
N15 C161 1.475(3) . ?
N21 C21 1.331(3) . ?
N21 N22 1.378(3) . ?
N22 C23 1.380(3) . ?
N22 C24 1.415(3) . ?
N23 C27 1.339(3) . ?
N23 C24 1.352(3) . ?
N24 C27 1.311(3) . ?
N24 C26 1.364(3) . ?
N25 C26 1.348(3) . ?
N25 C264 1.463(4) . ?
N25 C261 1.471(3) . ?
C11 C12 1.412(3) . ?
C11 C111 1.470(3) . ?
C12 C13 1.365(3) . ?
C12 H12 0.9500 . ?
C13 C131 1.480(3) . ?
C14 C15 1.359(3) . ?
C15 C16 1.412(3) . ?
C15 H15 0.9500 . ?
C17 H17 0.9500 . ?
C21 C22 1.413(3) . ?
C21 C211 1.476(3) . ?
C22 C23 1.361(3) . ?
C22 H22 0.9500 . ?
C23 C231 1.480(3) . ?
C24 C25 1.358(3) . ?
C25 C26 1.408(4) . ?
C25 H25 0.9500 . ?
C27 H27 0.9500 . ?
C111 C112 1.392(4) . ?
C111 C116 1.395(4) . ?
C112 C113 1.380(4) . ?
C112 H112 0.9500 . ?
C113 C114 1.384(4) . ?
C113 H113 0.9500 . ?
C114 C115 1.383(4) . ?
C114 H114 0.9500 . ?
C115 C116 1.394(4) . ?
C115 H115 0.9500 . ?
C116 H116 0.9500 . ?
C131 C132 1.392(3) . ?
C131 C136 1.398(4) . ?
C132 C133 1.393(4) . ?
C132 H132 0.9500 . ?
C133 C134 1.380(4) . ?
C133 H133 0.9500 . ?
C134 C135 1.378(4) . ?
C134 H134 0.9500 . ?
C135 C136 1.381(4) . ?
C135 H135 0.9500 . ?
C136 H136 0.9500 . ?
C161 C162 1.513(4) . ?
C161 H16A 0.9900 . ?
C161 H16B 0.9900 . ?
C162 H16C 0.9900 . ?
C162 H16D 0.9900 . ?
C163 C164 1.511(4) . ?
C163 H16E 0.9900 . ?
C163 H16F 0.9900 . ?
C164 H16G 0.9900 . ?
C164 H16H 0.9900 . ?
C211 C212 1.391(4) . ?
C211 C216 1.395(4) . ?
C212 C213 1.389(4) . ?
C212 H212 0.9500 . ?
C213 C214 1.381(4) . ?
C213 H213 0.9500 . ?
C214 C215 1.382(4) . ?
C214 H214 0.9500 . ?
C215 C216 1.388(4) . ?
C215 H215 0.9500 . ?
C216 H216 0.9500 . ?
C231 C232 1.388(4) . ?
C231 C236 1.397(3) . ?
C232 C233 1.387(4) . ?
C232 H232 0.9500 . ?
C233 C234 1.377(4) . ?
C233 H233 0.9500 . ?
C234 C235 1.383(4) . ?
C234 H234 0.9500 . ?
C235 C236 1.385(4) . ?
C235 H235 0.9500 . ?
C236 H236 0.9500 . ?
C261 C262 1.485(4) . ?
C261 H26A 0.9900 . ?
C261 H26B 0.9900 . ?
C262 H26C 0.9900 . ?
C262 H26D 0.9900 . ?
C263 C264 1.491(4) . ?
C263 H26E 0.9900 . ?
C263 H26F 0.9900 . ?
C264 H26G 0.9900 . ?
C264 H26H 0.9900 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
Cu2 Br4 Cu3 70.293(16) . . ?
N13 Cu1 N23 177.80(9) . . ?
N13 Cu1 N11 79.32(8) . . ?
N23 Cu1 N11 99.26(8) . . ?
N13 Cu1 N21 105.34(8) . . ?
N23 Cu1 N21 76.57(8) . . ?
N11 Cu1 N21 102.71(8) . . ?
N13 Cu1 Br1 92.40(6) . . ?
N23 Cu1 Br1 88.28(6) . . ?
N11 Cu1 Br1 156.53(6) . . ?
N21 Cu1 Br1 100.65(6) . . ?
Br2 Cu2 Br4 125.080(12) . 2 ?
Br2 Cu2 Br4 125.080(12) . . ?
Br4 Cu2 Br4 109.84(2) 2 . ?
Br2 Cu2 Cu3 180.0 . . ?
Br4 Cu2 Cu3 54.920(12) 2 . ?
Br4 Cu2 Cu3 54.920(12) . . ?
Br3 Cu3 Br4 125.213(12) . 2 ?
Br3 Cu3 Br4 125.213(12) . . ?
Br4 Cu3 Br4 109.57(2) 2 . ?
Br3 Cu3 Cu2 180.0 . . ?
Br4 Cu3 Cu2 54.787(12) 2 . ?
Br4 Cu3 Cu2 54.787(12) . . ?
C162 O11 C163 109.7(2) . . ?
C262 O21 C263 110.2(2) . . ?
C11 N11 N12 105.13(19) . . ?
C11 N11 Cu1 142.58(16) . . ?
N12 N11 Cu1 106.82(14) . . ?
C13 N12 N11 111.5(2) . . ?
C13 N12 C14 131.6(2) . . ?
N11 N12 C14 115.67(19) . . ?
C17 N13 C14 115.3(2) . . ?
C17 N13 Cu1 127.15(17) . . ?
C14 N13 Cu1 116.80(16) . . ?
C17 N14 C16 117.0(2) . . ?
C16 N15 C164 119.5(2) . . ?
C16 N15 C161 120.3(2) . . ?
C164 N15 C161 115.4(2) . . ?
C21 N21 N22 105.49(19) . . ?
C21 N21 Cu1 134.25(16) . . ?
N22 N21 Cu1 103.82(14) . . ?
N21 N22 C23 111.17(19) . . ?
N21 N22 C24 116.58(19) . . ?
C23 N22 C24 132.1(2) . . ?
C27 N23 C24 115.8(2) . . ?
C27 N23 Cu1 125.47(17) . . ?
C24 N23 Cu1 118.22(16) . . ?
C27 N24 C26 116.4(2) . . ?
C26 N25 C264 121.6(2) . . ?
C26 N25 C261 123.7(2) . . ?
C264 N25 C261 113.1(2) . . ?
N11 C11 C12 110.3(2) . . ?
N11 C11 C111 121.4(2) . . ?
C12 C11 C111 128.3(2) . . ?
C13 C12 C11 106.9(2) . . ?
C13 C12 H12 126.5 . . ?
C11 C12 H12 126.5 . . ?
C12 C13 N12 106.1(2) . . ?
C12 C13 C131 131.9(2) . . ?
N12 C13 C131 121.6(2) . . ?
N13 C14 C15 123.8(2) . . ?
N13 C14 N12 112.7(2) . . ?
C15 C14 N12 123.4(2) . . ?
C14 C15 C16 116.5(2) . . ?
C14 C15 H15 121.8 . . ?
C16 C15 H15 121.8 . . ?
N15 C16 N14 117.2(2) . . ?
N15 C16 C15 122.0(2) . . ?
N14 C16 C15 120.8(2) . . ?
N14 C17 N13 126.7(2) . . ?
N14 C17 H17 116.7 . . ?
N13 C17 H17 116.7 . . ?
N21 C21 C22 110.2(2) . . ?
N21 C21 C211 120.8(2) . . ?
C22 C21 C211 128.9(2) . . ?
C23 C22 C21 107.2(2) . . ?
C23 C22 H22 126.4 . . ?
C21 C22 H22 126.4 . . ?
C22 C23 N22 105.9(2) . . ?
C22 C23 C231 128.4(2) . . ?
N22 C23 C231 125.6(2) . . ?
N23 C24 C25 122.4(2) . . ?
N23 C24 N22 113.8(2) . . ?
C25 C24 N22 123.7(2) . . ?
C24 C25 C26 117.4(2) . . ?
C24 C25 H25 121.3 . . ?
C26 C25 H25 121.3 . . ?
N25 C26 N24 116.4(2) . . ?
N25 C26 C25 123.0(2) . . ?
N24 C26 C25 120.6(2) . . ?
N24 C27 N23 127.3(2) . . ?
N24 C27 H27 116.3 . . ?
N23 C27 H27 116.3 . . ?
C112 C111 C116 119.3(2) . . ?
C112 C111 C11 119.8(2) . . ?
C116 C111 C11 120.9(2) . . ?
C113 C112 C111 120.4(3) . . ?
C113 C112 H112 119.8 . . ?
C111 C112 H112 119.8 . . ?
C112 C113 C114 120.1(3) . . ?
C112 C113 H113 119.9 . . ?
C114 C113 H113 119.9 . . ?
C115 C114 C113 120.2(3) . . ?
C115 C114 H114 119.9 . . ?
C113 C114 H114 119.9 . . ?
C114 C115 C116 119.9(3) . . ?
C114 C115 H115 120.1 . . ?
C116 C115 H115 120.1 . . ?
C115 C116 C111 120.0(3) . . ?
C115 C116 H116 120.0 . . ?
C111 C116 H116 120.0 . . ?
C132 C131 C136 119.5(2) . . ?
C132 C131 C13 121.9(2) . . ?
C136 C131 C13 118.6(2) . . ?
C131 C132 C133 119.6(3) . . ?
C131 C132 H132 120.2 . . ?
C133 C132 H132 120.2 . . ?
C134 C133 C132 120.2(3) . . ?
C134 C133 H133 119.9 . . ?
C132 C133 H133 119.9 . . ?
C135 C134 C133 120.4(3) . . ?
C135 C134 H134 119.8 . . ?
C133 C134 H134 119.8 . . ?
C134 C135 C136 120.2(3) . . ?
C134 C135 H135 119.9 . . ?
C136 C135 H135 119.9 . . ?
C135 C136 C131 120.2(2) . . ?
C135 C136 H136 119.9 . . ?
C131 C136 H136 119.9 . . ?
N15 C161 C162 110.1(2) . . ?
N15 C161 H16A 109.6 . . ?
C162 C161 H16A 109.6 . . ?
N15 C161 H16B 109.6 . . ?
C162 C161 H16B 109.6 . . ?
H16A C161 H16B 108.2 . . ?
O11 C162 C161 111.6(2) . . ?
O11 C162 H16C 109.3 . . ?
C161 C162 H16C 109.3 . . ?
O11 C162 H16D 109.3 . . ?
C161 C162 H16D 109.3 . . ?
H16C C162 H16D 108.0 . . ?
O11 C163 C164 111.9(2) . . ?
O11 C163 H16E 109.2 . . ?
C164 C163 H16E 109.2 . . ?
O11 C163 H16F 109.2 . . ?
C164 C163 H16F 109.2 . . ?
H16E C163 H16F 107.9 . . ?
N15 C164 C163 110.6(2) . . ?
N15 C164 H16G 109.5 . . ?
C163 C164 H16G 109.5 . . ?
N15 C164 H16H 109.5 . . ?
C163 C164 H16H 109.5 . . ?
H16G C164 H16H 108.1 . . ?
C212 C211 C216 118.9(2) . . ?
C212 C211 C21 120.4(2) . . ?
C216 C211 C21 120.7(2) . . ?
C213 C212 C211 120.5(3) . . ?
C213 C212 H212 119.7 . . ?
C211 C212 H212 119.7 . . ?
C214 C213 C212 119.9(3) . . ?
C214 C213 H213 120.1 . . ?
C212 C213 H213 120.1 . . ?
C213 C214 C215 120.5(3) . . ?
C213 C214 H214 119.8 . . ?
C215 C214 H214 119.8 . . ?
C214 C215 C216 119.7(3) . . ?
C214 C215 H215 120.2 . . ?
C216 C215 H215 120.2 . . ?
C215 C216 C211 120.6(3) . . ?
C215 C216 H216 119.7 . . ?
C211 C216 H216 119.7 . . ?
C232 C231 C236 119.2(2) . . ?
C232 C231 C23 118.6(2) . . ?
C236 C231 C23 122.2(2) . . ?
C233 C232 C231 120.1(3) . . ?
C233 C232 H232 120.0 . . ?
C231 C232 H232 120.0 . . ?
C234 C233 C232 120.6(3) . . ?
C234 C233 H233 119.7 . . ?
C232 C233 H233 119.7 . . ?
C233 C234 C235 119.7(2) . . ?
C233 C234 H234 120.1 . . ?
C235 C234 H234 120.1 . . ?
C234 C235 C236 120.3(3) . . ?
C234 C235 H235 119.9 . . ?
C236 C235 H235 119.9 . . ?
C235 C236 C231 120.1(3) . . ?
C235 C236 H236 119.9 . . ?
C231 C236 H236 119.9 . . ?
N25 C261 C262 110.0(2) . . ?
N25 C261 H26A 109.7 . . ?
C262 C261 H26A 109.7 . . ?
N25 C261 H26B 109.7 . . ?
C262 C261 H26B 109.7 . . ?
H26A C261 H26B 108.2 . . ?
O21 C262 C261 113.6(3) . . ?
O21 C262 H26C 108.8 . . ?
C261 C262 H26C 108.8 . . ?
O21 C262 H26D 108.8 . . ?
C261 C262 H26D 108.8 . . ?
H26C C262 H26D 107.7 . . ?
O21 C263 C264 112.7(3) . . ?
O21 C263 H26E 109.1 . . ?
C264 C263 H26E 109.1 . . ?
O21 C263 H26F 109.1 . . ?
C264 C263 H26F 109.1 . . ?
H26E C263 H26F 107.8 . . ?
N25 C264 C263 109.7(2) . . ?
N25 C264 H26G 109.7 . . ?
C263 C264 H26G 109.7 . . ?
N25 C264 H26H 109.7 . . ?
C263 C264 H26H 109.7 . . ?
H26G C264 H26H 108.2 . . ?

_diffrn_measured_fraction_theta_max 1.000
_diffrn_reflns_theta_full        25.50
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         0.643
_refine_diff_density_min         -0.588
_refine_diff_density_rms         0.084
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_mbb_077b
_database_code_depnum_ccdc_archive 'CCDC 1424215'
_audit_update_record             
;
2015-09-14 deposited with the CCDC.
2015-11-09 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         'C23 H21 N5 O'
_chemical_formula_sum            'C23 H21 N5 O'
_chemical_melting_point          ?

_exptl_crystal_description       prism
_exptl_crystal_colour            colorless

_diffrn_ambient_temperature      150(2)
_chemical_formula_weight         383.45

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21/c'
_symmetry_int_tables_number      14
_chemical_absolute_configuration ?
_symmetry_space_group_name_Hall  '-P 2ybc'

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   11.6372(11)
_cell_length_b                   7.5691(6)
_cell_length_c                   21.511(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 94.403(3)
_cell_angle_gamma                90.00
_cell_volume                     1889.2(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    4499
_cell_measurement_theta_min      2.68
_cell_measurement_theta_max      26.37
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.15
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.348
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             808
_exptl_absorpt_coefficient_mu    0.086

_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9787
_exptl_absorpt_correction_T_max  0.9872
_exptl_absorpt_process_details   'SADABS (Bruker, 2004)'

_exptl_special_details           
; 
 ? 
;


_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker Nonius X8Apex CCD area-detector'
_diffrn_measurement_method       'φ scans'
_diffrn_detector_area_resol_mean 25
_diffrn_standards_number         0
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        0
_diffrn_reflns_number            13728
_diffrn_reflns_av_R_equivalents  0.0274
_diffrn_reflns_av_sigmaI/netI    0.0269
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_theta_min         1.76
_diffrn_reflns_theta_max         26.37
_reflns_number_total             3869
_reflns_number_gt                3080
_reflns_threshold_expression     >2σ(I)


_computing_data_collection       'APEX2 (Bruker, 2004)'
_computing_cell_refinement       'SAINT (Bruker, 2004)'
_computing_data_reduction        'SAINT (Bruker, 2004)'
_computing_structure_solution    'SHELXTL (Bruker, 2004)'
_computing_structure_refinement  'SHELXTL (Bruker, 2004)'
_computing_molecular_graphics    'SHELXTL (Bruker, 2004)'
_computing_publication_material  'SHELXTL (Bruker, 2004)'

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0475P)²+0.2950P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3869
_refine_ls_number_parameters     262
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0510
_refine_ls_R_factor_gt           0.0360
_refine_ls_wR_factor_ref         0.0918
_refine_ls_wR_factor_gt          0.0871
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_restrained_S_all      1.047
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O11 O 0.10423(8) 0.50497(13) 0.16501(4) 0.0301(2) Uani 1 1 d . . .
N11 N 0.63599(9) 0.80691(13) 0.03148(5) 0.0185(2) Uani 1 1 d . . .
N12 N 0.57850(9) 0.80603(13) -0.02628(5) 0.0175(2) Uani 1 1 d . . .
N13 N 0.41916(9) 0.69796(14) -0.08804(5) 0.0220(2) Uani 1 1 d . . .
N14 N 0.24869(9) 0.60272(13) -0.04165(5) 0.0211(2) Uani 1 1 d . . .
N15 N 0.23573(9) 0.60284(14) 0.06526(5) 0.0199(2) Uani 1 1 d . . .
C11 C 0.73605(10) 0.88556(15) 0.02421(6) 0.0169(3) Uani 1 1 d . . .
C12 C 0.74380(10) 0.93504(15) -0.03863(6) 0.0180(3) Uani 1 1 d . . .
H12 H 0.8071 0.9917 -0.0557 0.022 Uiso 1 1 calc R . .
C13 C 0.64241(11) 0.88550(15) -0.07021(5) 0.0171(3) Uani 1 1 d . . .
C14 C 0.46666(10) 0.72999(15) -0.03061(6) 0.0169(3) Uani 1 1 d . . .
C15 C 0.41425(10) 0.69497(15) 0.02312(6) 0.0178(3) Uani 1 1 d . . .
H15 H 0.4528 0.7131 0.0632 0.021 Uiso 1 1 calc R . .
C16 C 0.30096(10) 0.63108(15) 0.01583(6) 0.0173(3) Uani 1 1 d . . .
C17 C 0.31192(11) 0.63710(17) -0.08899(6) 0.0238(3) Uani 1 1 d . . .
H17 H 0.2753 0.6151 -0.1293 0.029 Uiso 1 1 calc R . .
C111 C 0.81739(10) 0.91646(16) 0.07902(6) 0.0184(3) Uani 1 1 d . . .
C112 C 0.90836(11) 1.03541(17) 0.07629(6) 0.0230(3) Uani 1 1 d . . .
H112 H 0.9219 1.0907 0.0379 0.028 Uiso 1 1 calc R . .
C113 C 0.97932(11) 1.07349(18) 0.12950(7) 0.0274(3) Uani 1 1 d . . .
H113 H 1.0405 1.1558 0.1274 0.033 Uiso 1 1 calc R . .
C114 C 0.96134(11) 0.99222(19) 0.18561(6) 0.0279(3) Uani 1 1 d . . .
H114 H 1.0098 1.0190 0.2220 0.033 Uiso 1 1 calc R . .
C115 C 0.87234(11) 0.87166(18) 0.18850(6) 0.0258(3) Uani 1 1 d . . .
H115 H 0.8603 0.8147 0.2268 0.031 Uiso 1 1 calc R . .
C116 C 0.80093(11) 0.83396(16) 0.13577(6) 0.0212(3) Uani 1 1 d . . .
H116 H 0.7401 0.7511 0.1382 0.025 Uiso 1 1 calc R . .
C131 C 0.60729(10) 0.92947(15) -0.13596(5) 0.0172(3) Uani 1 1 d . . .
C132 C 0.68960(11) 0.91220(16) -0.17944(6) 0.0204(3) Uani 1 1 d . . .
H132 H 0.7613 0.8569 -0.1677 0.024 Uiso 1 1 calc R . .
C133 C 0.66751(12) 0.97528(17) -0.23993(6) 0.0250(3) Uani 1 1 d . . .
H133 H 0.7245 0.9639 -0.2690 0.030 Uiso 1 1 calc R . .
C134 C 0.56336(12) 1.05424(17) -0.25800(6) 0.0266(3) Uani 1 1 d . . .
H134 H 0.5485 1.0978 -0.2993 0.032 Uiso 1 1 calc R . .
C135 C 0.48039(12) 1.06920(17) -0.21506(6) 0.0249(3) Uani 1 1 d . . .
H135 H 0.4081 1.1217 -0.2274 0.030 Uiso 1 1 calc R . .
C136 C 0.50190(11) 1.00864(16) -0.15463(6) 0.0207(3) Uani 1 1 d . . .
H136 H 0.4447 1.0210 -0.1257 0.025 Uiso 1 1 calc R . .
C161 C 0.29019(11) 0.58498(17) 0.12873(6) 0.0225(3) Uani 1 1 d . . .
H16A H 0.3535 0.6720 0.1353 0.027 Uiso 1 1 calc R . .
H16B H 0.3236 0.4652 0.1343 0.027 Uiso 1 1 calc R . .
C162 C 0.20275(12) 0.61529(19) 0.17605(6) 0.0285(3) Uani 1 1 d . . .
H16C H 0.2391 0.5916 0.2184 0.034 Uiso 1 1 calc R . .
H16D H 0.1782 0.7405 0.1744 0.034 Uiso 1 1 calc R . .
C163 C 0.04841(11) 0.54896(18) 0.10580(6) 0.0248(3) Uani 1 1 d . . .
H16E H 0.0277 0.6758 0.1052 0.030 Uiso 1 1 calc R . .
H16F H -0.0236 0.4796 0.0989 0.030 Uiso 1 1 calc R . .
C164 C 0.12558(11) 0.51094(17) 0.05426(6) 0.0231(3) Uani 1 1 d . . .
H16G H 0.1394 0.3821 0.0519 0.028 Uiso 1 1 calc R . .
H16H H 0.0871 0.5496 0.0139 0.028 Uiso 1 1 calc R . .


_geom_special_details            
; 
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O11 C162 1.4235(16) . ?
O11 C163 1.4241(15) . ?
N11 C11 1.3276(15) . ?
N11 N12 1.3652(14) . ?
N12 C13 1.3841(15) . ?
N12 C14 1.4196(15) . ?
N13 C17 1.3290(16) . ?
N13 C14 1.3364(15) . ?
N14 C17 1.3271(16) . ?
N14 C16 1.3527(15) . ?
N15 C16 1.3697(16) . ?
N15 C164 1.4616(16) . ?
N15 C161 1.4669(15) . ?
C11 C12 1.4124(17) . ?
C11 C111 1.4729(17) . ?
C12 C13 1.3678(17) . ?
C12 H12 0.9500 . ?
C13 C131 1.4798(16) . ?
C14 C15 1.3733(17) . ?
C15 C16 1.4018(17) . ?
C15 H15 0.9500 . ?
C17 H17 0.9500 . ?
C111 C112 1.3945(18) . ?
C111 C116 1.3973(17) . ?
C112 C113 1.3892(18) . ?
C112 H112 0.9500 . ?
C113 C114 1.3850(19) . ?
C113 H113 0.9500 . ?
C114 C115 1.3853(19) . ?
C114 H114 0.9500 . ?
C115 C116 1.3834(18) . ?
C115 H115 0.9500 . ?
C116 H116 0.9500 . ?
C131 C132 1.3953(17) . ?
C131 C136 1.3960(17) . ?
C132 C133 1.3912(17) . ?
C132 H132 0.9500 . ?
C133 C134 1.3802(19) . ?
C133 H133 0.9500 . ?
C134 C135 1.3911(19) . ?
C134 H134 0.9500 . ?
C135 C136 1.3831(18) . ?
C135 H135 0.9500 . ?
C136 H136 0.9500 . ?
C161 C162 1.5109(18) . ?
C161 H16A 0.9900 . ?
C161 H16B 0.9900 . ?
C162 H16C 0.9900 . ?
C162 H16D 0.9900 . ?
C163 C164 1.5071(17) . ?
C163 H16E 0.9900 . ?
C163 H16F 0.9900 . ?
C164 H16G 0.9900 . ?
C164 H16H 0.9900 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C162 O11 C163 108.56(10) . . ?
C11 N11 N12 105.55(9) . . ?
N11 N12 C13 111.58(10) . . ?
N11 N12 C14 116.38(9) . . ?
C13 N12 C14 132.03(10) . . ?
C17 N13 C14 113.48(11) . . ?
C17 N14 C16 115.69(11) . . ?
C16 N15 C164 118.69(10) . . ?
C16 N15 C161 120.75(10) . . ?
C164 N15 C161 114.69(10) . . ?
N11 C11 C12 110.65(11) . . ?
N11 C11 C111 119.51(11) . . ?
C12 C11 C111 129.77(11) . . ?
C13 C12 C11 106.65(11) . . ?
C13 C12 H12 126.7 . . ?
C11 C12 H12 126.7 . . ?
C12 C13 N12 105.57(10) . . ?
C12 C13 C131 125.27(11) . . ?
N12 C13 C131 128.82(11) . . ?
N13 C14 C15 124.34(11) . . ?
N13 C14 N12 116.50(10) . . ?
C15 C14 N12 119.16(11) . . ?
C14 C15 C16 116.57(11) . . ?
C14 C15 H15 121.7 . . ?
C16 C15 H15 121.7 . . ?
N14 C16 N15 116.60(11) . . ?
N14 C16 C15 120.66(11) . . ?
N15 C16 C15 122.66(11) . . ?
N14 C17 N13 129.16(12) . . ?
N14 C17 H17 115.4 . . ?
N13 C17 H17 115.4 . . ?
C112 C111 C116 118.74(12) . . ?
C112 C111 C11 120.81(11) . . ?
C116 C111 C11 120.37(11) . . ?
C113 C112 C111 120.29(12) . . ?
C113 C112 H112 119.9 . . ?
C111 C112 H112 119.9 . . ?
C114 C113 C112 120.40(12) . . ?
C114 C113 H113 119.8 . . ?
C112 C113 H113 119.8 . . ?
C113 C114 C115 119.68(12) . . ?
C113 C114 H114 120.2 . . ?
C115 C114 H114 120.2 . . ?
C116 C115 C114 120.22(12) . . ?
C116 C115 H115 119.9 . . ?
C114 C115 H115 119.9 . . ?
C115 C116 C111 120.67(12) . . ?
C115 C116 H116 119.7 . . ?
C111 C116 H116 119.7 . . ?
C132 C131 C136 118.72(11) . . ?
C132 C131 C13 117.79(11) . . ?
C136 C131 C13 122.92(11) . . ?
C133 C132 C131 120.51(12) . . ?
C133 C132 H132 119.7 . . ?
C131 C132 H132 119.7 . . ?
C134 C133 C132 120.48(12) . . ?
C134 C133 H133 119.8 . . ?
C132 C133 H133 119.8 . . ?
C133 C134 C135 119.17(12) . . ?
C133 C134 H134 120.4 . . ?
C135 C134 H134 120.4 . . ?
C136 C135 C134 120.82(12) . . ?
C136 C135 H135 119.6 . . ?
C134 C135 H135 119.6 . . ?
C135 C136 C131 120.28(12) . . ?
C135 C136 H136 119.9 . . ?
C131 C136 H136 119.9 . . ?
N15 C161 C162 110.36(11) . . ?
N15 C161 H16A 109.6 . . ?
C162 C161 H16A 109.6 . . ?
N15 C161 H16B 109.6 . . ?
C162 C161 H16B 109.6 . . ?
H16A C161 H16B 108.1 . . ?
O11 C162 C161 111.96(11) . . ?
O11 C162 H16C 109.2 . . ?
C161 C162 H16C 109.2 . . ?
O11 C162 H16D 109.2 . . ?
C161 C162 H16D 109.2 . . ?
H16C C162 H16D 107.9 . . ?
O11 C163 C164 110.90(11) . . ?
O11 C163 H16E 109.5 . . ?
C164 C163 H16E 109.5 . . ?
O11 C163 H16F 109.5 . . ?
C164 C163 H16F 109.5 . . ?
H16E C163 H16F 108.0 . . ?
N15 C164 C163 110.78(10) . . ?
N15 C164 H16G 109.5 . . ?
C163 C164 H16G 109.5 . . ?
N15 C164 H16H 109.5 . . ?
C163 C164 H16H 109.5 . . ?
H16G C164 H16H 108.1 . . ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        25.50
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.213
_refine_diff_density_min         -0.239
_refine_diff_density_rms         0.040
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_mbb_078
_database_code_depnum_ccdc_archive 'CCDC 1424216'
_audit_update_record             
;
2015-09-14 deposited with the CCDC.
2015-11-09 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         'C25 H18 Br3 Cu2 N4 O'
_chemical_formula_sum            'C25 H18 Br3 Cu2 N4 O'
_chemical_melting_point          ?
_exptl_crystal_description       prism
_exptl_crystal_colour            yellow

_diffrn_ambient_temperature      150(2)
_chemical_formula_weight         757.24

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21/n'
_symmetry_int_tables_number      14
_chemical_absolute_configuration ?
_symmetry_space_group_name_Hall  '-P 2yn'

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   8.2845(2)
_cell_length_b                   12.2544(3)
_cell_length_c                   24.6190(7)
_cell_angle_alpha                90.00
_cell_angle_beta                 92.9230(10)
_cell_angle_gamma                90.00
_cell_volume                     2496.11(11)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    7650
_cell_measurement_theta_min      2.35
_cell_measurement_theta_max      26.37
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.18
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    2.015
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1468
_exptl_absorpt_coefficient_mu    6.533

_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.2920
_exptl_absorpt_correction_T_max  0.3859
_exptl_absorpt_process_details   'SADABS (Bruker, 2004)'

_exptl_special_details           
; 
 ? 
;


_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker Nonius X8Apex CCD area-detector'
_diffrn_measurement_method       'φ scans'
_diffrn_detector_area_resol_mean 25
_diffrn_standards_number         0
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        0
_diffrn_reflns_number            16025
_diffrn_reflns_av_R_equivalents  0.0178
_diffrn_reflns_av_sigmaI/netI    0.0198
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_theta_min         1.66
_diffrn_reflns_theta_max         26.37
_reflns_number_total             5118
_reflns_number_gt                4485
_reflns_threshold_expression     >2σ(I)


_computing_data_collection       'APEX2 (Bruker, 2004)'
_computing_cell_refinement       'SAINT (Bruker, 2004)'
_computing_data_reduction        'SAINT (Bruker, 2004)'
_computing_structure_solution    'SHELXTL (Bruker, 2004)'
_computing_structure_refinement  'SHELXTL (Bruker, 2004)'
_computing_molecular_graphics    'SHELXTL (Bruker, 2004)'
_computing_publication_material  'SHELXTL (Bruker, 2004)'

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0210P)²+1.2457P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         5118
_refine_ls_number_parameters     316
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0258
_refine_ls_R_factor_gt           0.0195
_refine_ls_wR_factor_ref         0.0443
_refine_ls_wR_factor_gt          0.0432
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_restrained_S_all      1.038
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Br1 Br 0.12633(2) 0.725000(17) -0.083646(9) 0.01820(6) Uani 1 1 d . . .
Br2 Br 0.55686(3) 0.746083(19) -0.113094(9) 0.02541(6) Uani 1 1 d . . .
Br3 Br 1.13622(2) 0.551880(16) 0.065817(8) 0.01687(5) Uani 1 1 d . . .
Cu1 Cu 0.38432(3) 0.75820(2) -0.042167(10) 0.01661(6) Uani 1 1 d . . .
Cu2 Cu 0.88908(3) 0.45163(2) 0.037432(11) 0.01971(7) Uani 1 1 d . . .
O11 O 0.73506(18) 0.52677(12) 0.14387(6) 0.0213(3) Uani 1 1 d . . .
N11 N 0.33786(19) 0.85440(13) 0.02010(7) 0.0146(4) Uani 1 1 d . . .
N12 N 0.37222(19) 0.80545(13) 0.06964(7) 0.0139(4) Uani 1 1 d . . .
N13 N 0.5142(2) 0.68653(13) 0.01799(7) 0.0141(4) Uani 1 1 d . . .
N14 N 0.6960(2) 0.55314(13) 0.05403(7) 0.0150(4) Uani 1 1 d . . .
C17 C 0.6225(2) 0.60755(16) 0.01322(8) 0.0154(4) Uani 1 1 d . . .
H17 H 0.6497 0.5883 -0.0226 0.019 Uiso 1 1 calc R . .
C11 C 0.2787(2) 0.95264(16) 0.03026(9) 0.0155(4) Uani 1 1 d . . .
C12 C 0.2723(2) 0.96742(17) 0.08706(9) 0.0175(4) Uani 1 1 d . . .
H12 H 0.2344 1.0304 0.1049 0.021 Uiso 1 1 calc R . .
C13 C 0.3307(2) 0.87448(16) 0.11145(8) 0.0158(4) Uani 1 1 d . . .
C14 C 0.4766(2) 0.71559(16) 0.06882(8) 0.0125(4) Uani 1 1 d . . .
C15 C 0.5427(2) 0.66309(16) 0.11403(8) 0.0141(4) Uani 1 1 d . . .
H15 H 0.5135 0.6812 0.1497 0.017 Uiso 1 1 calc R . .
C16 C 0.6547(2) 0.58197(16) 0.10434(8) 0.0150(4) Uani 1 1 d . . .
C111 C 0.2319(2) 1.03034(16) -0.01320(9) 0.0160(4) Uani 1 1 d . . .
C112 C 0.2882(3) 1.02191(17) -0.06544(9) 0.0199(5) Uani 1 1 d . . .
H112 H 0.3602 0.9648 -0.0739 0.024 Uiso 1 1 calc R . .
C113 C 0.2391(3) 1.09686(18) -0.10505(9) 0.0230(5) Uani 1 1 d . . .
H113 H 0.2775 1.0910 -0.1406 0.028 Uiso 1 1 calc R . .
C114 C 0.1336(3) 1.18066(18) -0.09281(10) 0.0239(5) Uani 1 1 d . . .
H114 H 0.0988 1.2312 -0.1202 0.029 Uiso 1 1 calc R . .
C115 C 0.0797(3) 1.19053(18) -0.04104(10) 0.0248(5) Uani 1 1 d . . .
H115 H 0.0086 1.2482 -0.0326 0.030 Uiso 1 1 calc R . .
C116 C 0.1293(3) 1.11619(17) -0.00138(9) 0.0218(5) Uani 1 1 d . . .
H116 H 0.0929 1.1238 0.0344 0.026 Uiso 1 1 calc R . .
C131 C 0.3403(2) 0.84866(17) 0.17001(8) 0.0172(4) Uani 1 1 d . . .
C132 C 0.2638(3) 0.75714(17) 0.19039(9) 0.0211(5) Uani 1 1 d . . .
H132 H 0.2124 0.7061 0.1662 0.025 Uiso 1 1 calc R . .
C133 C 0.2632(3) 0.7409(2) 0.24615(10) 0.0282(5) Uani 1 1 d . . .
H133 H 0.2101 0.6789 0.2601 0.034 Uiso 1 1 calc R . .
C134 C 0.3391(3) 0.8142(2) 0.28150(10) 0.0330(6) Uani 1 1 d . . .
H134 H 0.3392 0.8020 0.3196 0.040 Uiso 1 1 calc R . .
C135 C 0.4152(3) 0.9053(2) 0.26173(10) 0.0327(6) Uani 1 1 d . . .
H135 H 0.4673 0.9556 0.2862 0.039 Uiso 1 1 calc R . .
C136 C 0.4151(3) 0.92310(19) 0.20602(9) 0.0239(5) Uani 1 1 d . . .
H136 H 0.4662 0.9861 0.1924 0.029 Uiso 1 1 calc R . .
C161 C 0.6888(3) 0.54523(17) 0.19763(9) 0.0194(5) Uani 1 1 d . . .
C162 C 0.5715(3) 0.47990(19) 0.21741(10) 0.0267(5) Uani 1 1 d . . .
H162 H 0.5224 0.4239 0.1956 0.032 Uiso 1 1 calc R . .
C163 C 0.5261(3) 0.4976(2) 0.27026(10) 0.0318(6) Uani 1 1 d . . .
H163 H 0.4449 0.4533 0.2850 0.038 Uiso 1 1 calc R . .
C164 C 0.5983(3) 0.5792(2) 0.30141(10) 0.0309(6) Uani 1 1 d . . .
H164 H 0.5657 0.5914 0.3374 0.037 Uiso 1 1 calc R . .
C165 C 0.7175(3) 0.6431(2) 0.28076(10) 0.0299(6) Uani 1 1 d . . .
H165 H 0.7673 0.6990 0.3025 0.036 Uiso 1 1 calc R . .
C166 C 0.7647(3) 0.62587(19) 0.22835(10) 0.0262(5) Uani 1 1 d . . .
H166 H 0.8477 0.6688 0.2138 0.031 Uiso 1 1 calc R . .


_geom_special_details            
; 
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Br1 Cu1 2.3567(3) . ?
Br1 Cu2 2.4516(3) 3_665 ?
Br2 Cu1 2.3170(3) . ?
Br3 Cu2 2.4584(3) . ?
Br3 Cu2 2.5402(3) 3_765 ?
Cu1 N11 1.9869(17) . ?
Cu1 N13 1.9898(17) . ?
Cu2 N14 2.0835(16) . ?
Cu2 Br1 2.4516(3) 3_665 ?
Cu2 Br3 2.5402(3) 3_765 ?
Cu2 Cu2 2.9199(5) 3_765 ?
O11 C16 1.335(2) . ?
O11 C161 1.415(3) . ?
N11 C11 1.328(2) . ?
N11 N12 1.376(2) . ?
N12 C13 1.389(3) . ?
N12 C14 1.401(2) . ?
N13 C17 1.329(2) . ?
N13 C14 1.353(3) . ?
N14 C17 1.328(3) . ?
N14 C16 1.349(3) . ?
C17 H17 0.9500 . ?
C11 C12 1.414(3) . ?
C11 C111 1.469(3) . ?
C12 C13 1.365(3) . ?
C12 H12 0.9500 . ?
C13 C131 1.474(3) . ?
C14 C15 1.375(3) . ?
C15 C16 1.389(3) . ?
C15 H15 0.9500 . ?
C111 C116 1.393(3) . ?
C111 C112 1.394(3) . ?
C112 C113 1.385(3) . ?
C112 H112 0.9500 . ?
C113 C114 1.391(3) . ?
C113 H113 0.9500 . ?
C114 C115 1.377(3) . ?
C114 H114 0.9500 . ?
C115 C116 1.382(3) . ?
C115 H115 0.9500 . ?
C116 H116 0.9500 . ?
C131 C132 1.394(3) . ?
C131 C136 1.395(3) . ?
C132 C133 1.387(3) . ?
C132 H132 0.9500 . ?
C133 C134 1.380(4) . ?
C133 H133 0.9500 . ?
C134 C135 1.382(4) . ?
C134 H134 0.9500 . ?
C135 C136 1.389(3) . ?
C135 H135 0.9500 . ?
C136 H136 0.9500 . ?
C161 C162 1.367(3) . ?
C161 C166 1.376(3) . ?
C162 C163 1.390(3) . ?
C162 H162 0.9500 . ?
C163 C164 1.378(3) . ?
C163 H163 0.9500 . ?
C164 C165 1.378(3) . ?
C164 H164 0.9500 . ?
C165 C166 1.383(3) . ?
C165 H165 0.9500 . ?
C166 H166 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
Cu1 Br1 Cu2 91.081(11) . 3_665 ?
Cu2 Br3 Cu2 71.463(11) . 3_765 ?
N11 Cu1 N13 78.83(7) . . ?
N11 Cu1 Br2 140.42(5) . . ?
N13 Cu1 Br2 101.64(5) . . ?
N11 Cu1 Br1 103.28(5) . . ?
N13 Cu1 Br1 133.65(5) . . ?
Br2 Cu1 Br1 104.069(13) . . ?
N14 Cu2 Br1 112.17(5) . 3_665 ?
N14 Cu2 Br3 106.42(5) . . ?
Br1 Cu2 Br3 111.813(12) 3_665 . ?
N14 Cu2 Br3 100.45(5) . 3_765 ?
Br1 Cu2 Br3 116.478(12) 3_665 3_765 ?
Br3 Cu2 Br3 108.537(11) . 3_765 ?
N14 Cu2 Cu2 113.31(5) . 3_765 ?
Br1 Cu2 Cu2 134.485(15) 3_665 3_765 ?
Br3 Cu2 Cu2 55.571(10) . 3_765 ?
Br3 Cu2 Cu2 52.966(10) 3_765 3_765 ?
C16 O11 C161 116.88(16) . . ?
C11 N11 N12 106.85(16) . . ?
C11 N11 Cu1 140.42(15) . . ?
N12 N11 Cu1 112.69(12) . . ?
N11 N12 C13 110.10(16) . . ?
N11 N12 C14 115.46(16) . . ?
C13 N12 C14 131.73(17) . . ?
C17 N13 C14 117.51(17) . . ?
C17 N13 Cu1 126.69(14) . . ?
C14 N13 Cu1 115.54(13) . . ?
C17 N14 C16 115.81(17) . . ?
C17 N14 Cu2 118.59(14) . . ?
C16 N14 Cu2 124.74(14) . . ?
N14 C17 N13 125.77(19) . . ?
N14 C17 H17 117.1 . . ?
N13 C17 H17 117.1 . . ?
N11 C11 C12 109.58(18) . . ?
N11 C11 C111 122.44(19) . . ?
C12 C11 C111 127.98(18) . . ?
C13 C12 C11 107.35(18) . . ?
C13 C12 H12 126.3 . . ?
C11 C12 H12 126.3 . . ?
C12 C13 N12 106.12(18) . . ?
C12 C13 C131 127.57(18) . . ?
N12 C13 C131 126.23(18) . . ?
N13 C14 C15 121.65(18) . . ?
N13 C14 N12 113.06(17) . . ?
C15 C14 N12 125.22(18) . . ?
C14 C15 C16 115.97(19) . . ?
C14 C15 H15 122.0 . . ?
C16 C15 H15 122.0 . . ?
O11 C16 N14 113.34(17) . . ?
O11 C16 C15 123.39(18) . . ?
N14 C16 C15 123.25(19) . . ?
C116 C111 C112 119.0(2) . . ?
C116 C111 C11 118.60(19) . . ?
C112 C111 C11 122.38(18) . . ?
C113 C112 C111 120.0(2) . . ?
C113 C112 H112 120.0 . . ?
C111 C112 H112 120.0 . . ?
C112 C113 C114 120.1(2) . . ?
C112 C113 H113 119.9 . . ?
C114 C113 H113 119.9 . . ?
C115 C114 C113 120.1(2) . . ?
C115 C114 H114 119.9 . . ?
C113 C114 H114 119.9 . . ?
C114 C115 C116 119.8(2) . . ?
C114 C115 H115 120.1 . . ?
C116 C115 H115 120.1 . . ?
C115 C116 C111 120.9(2) . . ?
C115 C116 H116 119.6 . . ?
C111 C116 H116 119.6 . . ?
C132 C131 C136 119.5(2) . . ?
C132 C131 C13 121.46(19) . . ?
C136 C131 C13 118.75(19) . . ?
C133 C132 C131 119.8(2) . . ?
C133 C132 H132 120.1 . . ?
C131 C132 H132 120.1 . . ?
C134 C133 C132 120.4(2) . . ?
C134 C133 H133 119.8 . . ?
C132 C133 H133 119.8 . . ?
C133 C134 C135 120.3(2) . . ?
C133 C134 H134 119.8 . . ?
C135 C134 H134 119.8 . . ?
C134 C135 C136 119.8(2) . . ?
C134 C135 H135 120.1 . . ?
C136 C135 H135 120.1 . . ?
C135 C136 C131 120.2(2) . . ?
C135 C136 H136 119.9 . . ?
C131 C136 H136 119.9 . . ?
C162 C161 C166 122.5(2) . . ?
C162 C161 O11 118.1(2) . . ?
C166 C161 O11 119.4(2) . . ?
C161 C162 C163 118.2(2) . . ?
C161 C162 H162 120.9 . . ?
C163 C162 H162 120.9 . . ?
C164 C163 C162 120.2(2) . . ?
C164 C163 H163 119.9 . . ?
C162 C163 H163 119.9 . . ?
C163 C164 C165 120.4(2) . . ?
C163 C164 H164 119.8 . . ?
C165 C164 H164 119.8 . . ?
C164 C165 C166 119.9(2) . . ?
C164 C165 H165 120.0 . . ?
C166 C165 H165 120.0 . . ?
C161 C166 C165 118.7(2) . . ?
C161 C166 H166 120.7 . . ?
C165 C166 H166 120.7 . . ?

_diffrn_measured_fraction_theta_max 1.000
_diffrn_reflns_theta_full        25.50
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         0.446
_refine_diff_density_min         -0.286
_refine_diff_density_rms         0.069
